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 Dr. Eusebio Juaristi

áreas  de  Investigación

 

Análisis conformacional
Destacan sus estudios del efecto anomérico [E. Juaristi y G. Cuevas, “The Anomeric Effect”, CRC Press: Boca Raton, Fl (1995)], de las contribuciones entálpicas y entrópicas en equilibrios conformacionales [vease, por ejemplo: E. Juaristi, V. Labastida y S. Antúnez, “Enthalpic and Entropic Contributions to the Conformational Free Energies..." Journal of Organic Chemistry, 65, 969-973 (2000)] y el análisis conformacional de anillos de seis miembros [E. Juaristi, ed., “Conformational Behavior of Six-Membred Rings”, VCH: New York (1995)].

(1) E. Juaristi, G.A. Rosquete-Pina, M. Vázquez-Hernández y A.J. Mota, “Salt Effects on the Conformational Behavior of 5-Substituted 1,3-Dioxanes”, Pure & Appl. Chem., 75, 589-599 (2003).

(2) J.S. Cruz-Sánchez y E. Juaristi, “Contrasting Conformational Behavior of 5-Methylsulfonyl-1,3-dioxane and -1,3-Dithiane in the Minimization of Steric and Electrostatic Interactions”, Tetrahedron Lett., 43, 9369-9372 (2002).

(3) M. Vázquez-Hernández, G. Rosquete-Pina y E. Juaristi, “Salt Effects on the Conformational Behavior of 5-Carboxy- and 5-Hydroxy-1,3-Dioxane”, J. Org. Chem., 69 , 9063-9072 (2004).

(4) M. Sosa-Rivadeneyra, L. Quintero, C. Anaya de Parrodi, E. Juaristi y S. Bernés, “N,N’-bis [(R)-2-Hydroxy-2-phenylethyl ]-N,N’bis [(S)-1-phenylethyl ]pyridine-2,6-dicarboxamide. Stabilization of an Asymmetric Conformer Through the Formation of a Double Intramolecular Hydrogen Bond”, Acta Cryst. Sect. E, 61, 536-538 (2005).

(5) M. Hernández-Rodríguez y E. Juaristi, “Synthesis and Conformational Analysis of Chiral Ureas Incorporating N-1-Phenylethyl Groups. Manifestation of Allylic       1,3-Strain”, J. Phys. Org. Chem., 18, 792-799 (2005), (Número Especial dedicado al Prof. Otto Exner).

(6) R. Notario, M.V. Roux, G. Cuevas, J. Cárdenas, V. Leyva y E. Juaristi, “Computational Study of 1,3-Dithiane 1,1-Dioxide (1,3-Dithiane Sulfone). Rigorous Description of the Inversion Process and Manifestation of Stereoelectronic Effects on 1 JC-H Coupling”, Chem. Phys. Chem., 110, 7703-7712 (2006).

(7) G. Huelgas, S. Bernés, M. Sánchez, L. Quintero, E. Juaristi, C. Anaya de Parrodi y P. J. Walsh, “Síntesis and Dynamics of Atropisomeric (S)-N-(-Phenylelthyl)benzamides”, Tetrahedron, 63, 12655-12664 (2007)

(8) E. Juaristi, “Introducción a la Estereoquímica y al Análisis Conformacional”, 1000 ejemplares, El Colegio Nacional: México, 2007. ISBN: 970-640-333-7.

(9) Y. Liu, R. Melgar-Fernández y E. Juaristi,“Enantioselective Amination of -Phenyl -Cyanoacetate Catalyzed by Chiral Amines Incorporating the -Phenylethyl Auxiliary”, J. Org. Chem., 72, 1522-1525 (2007).

Estereoquímica
Pionero en México del desarrollo de la síntesis asimétrica. Publicaciones representativas:

(1) E. Juaristi, ed., “Enantioselective Synthesis of  -Amino Acids”, Wiley-VCH: New York, 1997,

(2) E. Juaristi y H. López-Ruiz, “Recent Advances in the Enantioselective Synthesis of  -Amino Acids”, Current Medicinal Chemistry, 6, 983-1004 (1999),

(3) “Recent Applications of -Phenylethylamine in the Preparation of Enantiopure Compounds”, Tetrahedron: Asymmetry, 10, 2441-2495 (1999).

(4) G. Cuevas y E. Juaristi, “Manifestation of Stereoelectronic Effects on the Calculated C-H Bond Lengths and Coupling Constants in Cyclohexane, Six-Membered Heterocycles, and Cyclohexanone Derivatives”, J. Am. Chem. Soc., 124, 13088-13096 (2002).

(5) A. Clara-Sosa, L. Pérez, M. Sánchez, R. Melgar-Fernández, E. Juaristi, L. Quintero y C. Anaya de Parrodi, “cis - and trans-N-(Benzylsulfinyl)hexahydrobenzoxazolidin-2-one as Novel Chiral Sulfinyl Transfer Reagents”, Tetrahedron, 60, 12147-12152 (2004).

(6) E. Juaristi, “Quiralidad: Izquierda y Derecha en Química”, Ciencia, 56, 43-54 (2005).

(7) E. Juaristi, “Fundamentos de la Síntesis Asimétrica”, Revista del Colegio Panameño de Químicos, 22, 3-10 (2005).

(8) E. Juaristi y C. Anaya de Parrodi,  “Chiral 1,2-Aminoalcohols and 1,2-Diamines Derived from Cyclohexene Oxide. Recent Applications in Asymmetric Synthesis”, Synlett, 2699-2715 (2006).

(9) E. Juaristi y L. García-Colín, “Un Camino Marcado por la Curiosidad, la Obstinación y la Casualidad”, El Colegio Nacional: México (2006), ISBN: 970-640-321-3.

(10) M. Hernández-Rodríguez y E. Juaristi, “Structurally Simple Chiral Thioureas as Chiral Solvating Agents in the Enantiodiscrimination of Carboxylic Acids”, Tetrahedron, 63, 7673-7678 (2007).

(11) G. Huelgas, S. Bernés, M. Sánchez, L. Quintero, E. Juaristi, C. Anaya de Parrodi y P. J. Walsh, “Síntesis and Dynamics of Atropisomeric (S)-N-(-Phenylelthyl)benzamides”, Tetrahedron, 63, 12655-12664 (2007).

(12) E. Juaristi, “Introducción a la Estereoquímica y al Análisis Conformacional”, 1000 ejemplares, El Colegio Nacional: México, 2007. ISBN: 970-640-333-7.

(13) Y. Liu, R. Melgar-Fernández y E. Juaristi,“Enantioselective Amination of -Phenyl -Cyanoacetate Catalyzed by Chiral Amines Incorporating the -Phenylethyl Auxiliary”, J. Org. Chem., 72, 1522-1525 (2007).
 
Fisicoquímica orgánica
Al iniciar en México el área de la fisicoquímica orgánica con énfasis en el análisis conformacional, el Dr. Juaristi ha desarrollado una línea de investigación hasta entonces ausente en nuestro país. A nivel docente,  se destacan :

(1) E. Juaristi, “Introducción a la Estereoquímica y al Análisis Conformacional”, Minal: México, 1989 y 1998,

(2) E. Juaristi, “Fisicoquímica Orgánica”, Minal: México, 1989 y 1998,

(3) E. Juaristi, “Introduction to Stereochemistry and Conformational Analysis”, Wiley: New York, 1991 y 2000.

(4) O. Muñoz-Muñiz y E. Juaristi, “Computational Determination of the Enthalpic and Entropic Contributions to the Conformational Preference of Monosubstituted Cyclohexanes. Molecular Mechanics, Semiempirical, Density Functional Theory Methods, and Ab Initio Calculations”, J. Phys. Org. Chem., 15, 808-819 (2002).

(5) G. Cuevas y E. Juaristi, “Manifestation of Stereoelectronic Effects on the Calculated Carbon-Hydrogen Bond Lengths and 1JC-H NMR Coupling Constants in Cyclohexane, Six-Membered Heterocycles, and Cyclohexanone Derivatives”, J. Am. Chem. Soc., 124 , 13088-13096 (2002).

(6) M.V. Roux, M. Temprado, P. Jiménez, J. Zeñón Dávalos, R. Notario, R. Guzmán-Mejía y E. Juaristi, “Calorimetric and Computational Study of Thiacyclohexane-1-oxide and 1,1-Dioxide (Thiane Sulfoxide and Thiane Sulfone). Enthalpies of Formation and the Energy of the S = O Bond”, J. Org. Chem. , 68, 1762-1770 (2003).

(7) M. Temprado, M.V. Roux, P. Jiménez, R. Guzmán-Mejía, E. Juaristi y J.S. Chicos, “Heat Capacities of Thiane Sulfones and Thiane Sulfoxide. Refining of Cp Group Values of Organosulfur Compounds and their Oxides”, Thermochimica Acta, 406,9-16(2003).

(8) J. Manríquez, E. Juaristi, O. Muñoz-Muñiz y L.A. Godínez, “QCM Study of the Aggregation of Starburst PAMAM Dendrimers on the Surface of Bare and Thiol-Modifies Gold Electrodes”, Langmuir, 19, 7315-7323 (2003).

(9) M.V. Roux, M. Temprado, P. Jiménez, R. Notario, R. Guzmán-Mejía y E. Juaristi, “Calorimetric and Computational Study of 1,3-Dithiacyclohexane 1,1-Dioxide (1,3-Dithiane Sulfone)”, J. Org. Chem. , 69, 1670-1675 (2004).

(10) M.A. Iglesias-Arteaga, E. Juaristi y F. González, “An Electrochemical Interpretation of the Mechanism of the Chemical Decarboxylation of 6-Carboxy-perhydropyrimidin-4-ones”, Tetrahedron, 60, 3605-3610 (2004).

(11) M.V. Roux, M.Temprado, P. Jiménez, J.Z. Dávalos, R. Notario, L. Garrido, R. Guzmán-Mejía y E. Juaristi, “Thermochemistry of 1,3-Dithiacyclohexane 1-Oxide (1,3-Dithiane Sulfoxide): A Calorimetric and Computational Study” , J. Org. Chem., 69, 5454-5459 (2004).

(12) E. Juaristi, R. Notario y M.V. Roux, “Calorimetric and Computational Study of Sulfur-Containing Six-Membered Rings”, Chem. Soc. Rev. , 34, 347-354 (2005).

(13) M. Temprado, M.V. Roux, P. Jiménez, R. Guzmán-Mejía y E. Juaristi, “Thermophysical Study by DSC of Some Sulfur Heterocyclic Compounds: Thiane and Thiophene Derivatives”, Thermochim. Acta, 441, 20-26 (2006).

(15) M.V. Roux, M. Temprado, P. Jiménez, R. Notario, R. Guzmán-Mejía y E. Juaristi,“Calorimetric and Computational Study of 1,4-Dithiacyclohexane 1,1-Dioxide (1,4-Dithiane Sulfone)”, J. Org. Chem., 71, 2581-2586 (2006).

(16) E. Bustos Bustos, M.G. García Jiménez, B.R. Díaz-Sánchez, E. Juaristi y L.A. Godínez, “Determination of Dopamine in Real Simples by Liquid Chromatography with Spectrometric Detection Ensambled to Electrochemical Detection Using Covalent Modified Glassy Carbon Electrodes with Composites of Starburst PAMAM Dendrimers and Metal Nanoparticles”, Talanta, 72, 1586-1592 (2007).

(17) E. Navarro, F.J. González, P.D. Astudillo, M. Vázquez-Hernández, M. Hernández-Rodríguez y E. Juaristi, “The Role of Alkali and Alkaline Earth Metal Ions on the Hydrolysis of 2-Ferrocenyl-1,3-dioxane in Acetonitrile Solutions”, Polish J. Chem., 81, 921-930 (2007).

(18) G. Huelgas, S. Bernés, M. Sánchez, L. Quintero, E. Juaristi, C. Anaya de Parrodi y P. J. Walsh, “Synthesis and Dynamics of Atropisomeric (S)-N-(-Phenylelthyl) benzamides”, Tetrahedron, 63, 12655-12664 (2007).

(19) E. Juaristi y G. Cuevas, “Manifestations of Stereoelectronic Interactions in 1JC-H One Bond Coupling Constants”, Acc. Chem. Res., 40, 961-970 (2007).

(20) E. Bustos Bustos, G. Reyes-Rangel, B.R. Díaz-Sánchez, J. Manríquez Rocha, E. Juaristi, T.W. Chapman y L.A. Godínez, “Minimization of Lateral Repulsive Interactions Between -Cyclodextrine Adsorbed on the Ferrocene-PAMAM Dendrimers Modified Electrodes” , J. Braz. Chem. Soc., 19, 1010-1016 (2008).

(21) Y. Bandala, I.A. Rivero, T. González, J. Aviña, y E. Juaristi,“Solid Phase Synthesis of Novel / -Tetrapeptides and Electrospray Ionization Mass Spectrometric Evaluation of Their Metal Cation Complexation Behavior”, J. Phys. Org. Chem., 21, 349-358 (2008).
 
Modelado Molecular
Muchos de los trabajos experimentales en el grupo de investigación del Dr. Juaristi se apoyan o complementan con estudios de modelado molecular, que permiten explicar los resultados observados o ayudan a proponer mecanismos de reacción. Ejemplos recientes:

(1) E. Juaristi, “Stable Ecipsed Conformations”, en Encyclopedia of Computational Chemistry, Wiley: New York, 1998,

(2) G. Cuevas, E. Juaristi y A. Vela, “Application of the SOS-DFTPT Method for the Calculation of  1JC-H Coupling Constants in Cyclohexane and 1,3-Diheterocyclohexanes.”, J. Phys. Chem., 103 , 932-937 (1999),

(3) J. Escalante, M.A. González-Tototzin, J. Aviña, O. Múñoz-Múñiz y E. Juaristi,“Synthesis of -Lactams and Cyclo--dipeptides from -Amino Acids. Experimental Observations and Theoretical Analysis”, Tetrahedron, 57, 1883-1890 (2001).

(4) V.M. Gutiérrez, G. Reyes, O. Muñoz y E. Juaristi, “Diastereoselective Alkylation of Dianions Derived from Chiral Analogs of   -Aminopropionic Acid”, Helv. Chim. Acta, 85, 4189-4199 (2002).

(5) M. Sosa-Rivadeneyra, O. Muñoz-Muñiz, C. Anaya de Parrodi, L. Quintero-Cortés y E. Juaristi, “Molecular Modelling of Salt (Lithium Chloride) Effects on the Enantiosslectivity of Diethylzinc Addition to Benzaldehyde in the Presence of Chiral -Aminoalcohols”, J. Org. Chem., 68, 2369-2375 (2003).

(6) M.V. Roux, M. Temprado, P. Jiménez, R. Notario, R. Guzmán-Mejía y E. Juaristi, “Calorimetric and Computational Study of 1,3-Dithiacyclohexane 1,1-Dioxide (1,3-Dithiane Sulfone)”, J. Org. Chem., 69, 1670-1675 (2004).

(7) K. Martínez-Mayorga, E. Juaristi y G. Cuevas, “Manifestation of Stereoelectronic Effects on the Calculated Carbon-Hydrogen Bond Lengths and One Bond 1 J C-H NMR Coupling Constants. Relative Acceptor Ability of the Carbonyl (C=O), Thiocarbonyl (C=S), and Methyledene (C=CH 2 ) Groups Towards C-H Donor Bonds”, J. Org. Chem., 69, 7266-7276 (2004).

(8) G. Cuevas, K. Martínez-Mayorga, M.C. Fernández-Alonso, J. Jiménez-Barbero, C.L. Perrin, E. Juaristi y N. López-Mora, “The Origin of One Bond C-H Coupling Constants in O-C-H Fragments: Not Primarily nO   s* C-H Delocalization”, Angew. Chem., Int. Ed ., 44, 2360-2364 (2005).

(9) M.V. Roux, M. Temprado, P. Jiménez, R. Notario, R. Guzmán-Mejía y E. Juaristi, “Calorimetric and Computational Study of 1,4-Dithiacyclohexane 1,1-Dioxide (1,4-Dithiane Sulfone)”, J. Org. Chem., 71, 2581-2586 (2006).

(10) R. Notario, M.V. Roux, G. Cuevas, J. Cárdenas, V. Leyva y E. Juaristi, “Computational Study of 1,3-Dithiane 1,1-Dioxide (1,3-Dithiane Sulfone)”. Rigorous Description of the Inversion Process and Manifestation of Stereoelectronic Effects on 1JC-H Coupling”, Chem. Phys. Chem., 110, 7703-7712 (2006).

(11) M.V. Roux, M. Temprado, P. Jiménez, R. Notario, R. Guzmán-Mejía y E. Juaristi, “Calorimetric and Computational Study of 1,3- and 1,4-Oxathiane Sulfones”, J. Org. Chem., 72, 1143-1147 (2007).

(12)Juaristi y G. Cuevas, “Manifestations of Stereoelectronic Interactions in 1JC-H One Bond Coupling Constants”, Acc. Chem. Res., 40, 961-970 (2007).
 
Química Heterocíclica
El grupo de investigación del Dr. Juaristi ha trabajado durante más de 20 años en el estudio conformational y en la aplicación en síntesis orgánica de compuestos heterocíclicos conteniendo azufre vease, por ejemplo:

(1) E. Juaristi, “Conformational Analysis of Six-Membered, Sulfur-Containing Saturated Heterocycles”, Acc. Chem. Res., 22, 357-364 (1989),

(2) E. Juaristi, “1-Benzoyl-2(S)- tert-butyl-3-methylpyrimidinone-4-one”, en Encyclopedia of Reagents for Organic Synthesis, L.A. Paquette, ed., Wiley: New York, July 4,(2002).

(3) E. Juaristi y M. Ordóñez, “Conformational Preference of the Sulfinyl Group in Six-Membered Heterocycles”, en Organosulfphur Chemistry, P. Page, ed., Academic Press: London, (1997) Capítulo 3, p. 63-95. .

(4) M.A. Iglesias-Arteaga, E. Castellanos y E. Juaristi, “Alternative Procedure for the Síntesis of Enantiopure 1-Benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one, a Useful Starting Material for the Enantioselective Synthesis of -Substituted -Amino Acids”, Tetrahedron: Asymmetry, 14, 577-580 (2003).

(5) I. Linzaga, J. Escalante, M. Muñoz y E. Juaristi, “NMR and X-Ray Crystallographic Studies of Axial and Equatorial 2-Ethoxy-2-oxo-1,4,2-oxazaphosphinane Derivatives”, Tetrahedron, 58, 8973-8978 (2002).

(6) M. Sosa-Rivadeneyra, L. Quintero, C. Anaya de Parrodi, S. Barnés, E. Castellanos y E. Juaristi, “Preparation and Diastereoselective Methylation of Enantiopure (S)-4-(1-Phenylethyl)-1,4-oxazin-2-ones”, Arkivoc (Número Especial dedicado a la Química Orgánica en México), 2003, 61-71 (2003).

(7) R. Melgar-Fernández, P. Demare, E. Hong, J. Escalante, O. Muñoz-Muñiz, E. Juaristi y I. Regla, “Synthesis and Cardiovascular Activity of Metoprolol Analogs”, Bioorg. Med. Chem. Lett., 14, 191-194 (2004).

(8) M.V. Roux, M. Temprado, P. Jiménez, R. Notario, R. Guzmán-Mejía y E. Juaristi, “Calorimetric and Computational Study of 1,3-Dithiacyclohexane 1,1-Dioxide (1,3-Dithiane Sulfone)”, J. Org. Chem., 69, 1670-1675 (2004).

(9) M.A. Iglesias-Arteaga, E. Juaristi y F. González, “An Electrochemical Interpretation of the Mechanism of the Chemical Decarboxylation of 6-Carboxy-perhydropyrimidin-4-ones”, Tetrahedron, 60 , 3605-3610 (2004).

(10)M. Sosa-Rivadeneyra, L. Quintero, C. Anaya de Parrodi, E. Juaristi y S. Bernés, “N,N’-bis [(R)-2-Hydroxy-2-phenylethyl]-N,N’bis [(S)-1-phenylethyl] pyridine-2,6-dicarboxamide. Stabilization of an Asymmetric Conformer Through the Formation of a Double Intramolecular Hydrogen Bond”, Acta Cryst. Sect. E, 61, 536-538 (2005).

(11) M. Temprado, M.V. Roux, P. Jiménez, R. Guzmán-Mejía y E. Juaristi, “Thermophysical Study by DSC of Some Sulfur Heterocyclic Compounds: Thiane and Thiophene Derivatives”, Thermochim. Acta, 441, 20-26 (2006).

(12) G. Reyes-Rangel, V. Marañón, C.G. Avila-Ortiz, C. Anaya, L. Quintero y E. Juaristi, “Enantioselective Synthesis of (R)-2-Amino-3-phosphonopropionic Acid, (R)-AP-3, Via Diastereoselective Azidation of (4S,5R)-trans-N-[Diethoxyphosphoryl)-propionyl]hexahydrobenzoxazolidin-2-one”, Tetrahedron, 62, 8404-8409 (2006).

(13) E. Juaristi, B.R.Díaz y J.L. Olivares, “Dioxa-, Oxathia- and Dithiazines”, en Comprehensive Heterocyclic Chemistry III, Elservier, Oxford, (2007); capítulo 9.10, pp.

(14) E. Navarro, F.J. González, P.D. Astudillo, M. Vázquez-Hernández, M. Hernández-Rodríguez y E. Juaristi, “The Role of Alkali and Alkaline Earth Metal Ions on the Hydrolysis of 2-Ferrocenyl-1,3-dioxane in Acetonitrile Solutions”, Polish J. Chem., 81, 921-930 (2007).

(15) B.R. Díaz-Sánchez, M.A. Iglesias-Arteaga, R. Melgar-Fernández y E. Juaristi, “Synthesis of 2-Substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones and Their Derivatization to Potential Precursors of a-Substituted -Amino Acids Utilizing the Sonogashira Coupling Reaction”, J. Org. Chem., 72, 4822-4825 (2007).

(16) A. R. Sting, D. Seebach, R. Melgar-Fernández y E. Juaristi, “(R,R)-2-t-Butyl-5-methyl-1,3-dioxolan-4-one: Update”, en Electronic Encyclopedia of Reagents for Organic Synthesis, D. Crich, Editor; Wiley: New York, (2007); pp. 1-12.
 
Resonancia Magnética Nuclear
Principalmente sus aplicaciones en la determinación de la conformación preferida de compuestos heterocíclicos. Por ejemplo:

(1) E. Juaristi, J. Guzmán, V.V. Kane y R.S. Glass, “1 H and 13 C NMR Studies of the Mono-S-oxides of 1,2-, 1,3-, and 1,4-Dithianes”, Tetrahedron, 40, 1477-1485 (1984),

(2) B.M. Pinto, D.B. Johnston, R. Nagelkerke, E. Juaristi y E.A. González, “Determination of the Nitrogen Lone Pair Orientation in 2-Benzoyl-5-methyl-5-aza-1,3-dithiacyclohexane”, Can. J. Chem., 67, 2067-2070 (1989),

(3) E. Juaristi, G. Cuevas y A. Vela, “Stereoelectronic Interpretation for the Anomalous 1H NMR Chemical Shifts and One-Bond C-H Coupling Constants”, J. Am. Chem. Soc., 116, 5796-5804 (1994),

(4) C. Anaya de Parrodi, G.E. Moreno, L. Quintero y E. Juaristi, “Application of Phosphorylated Reagents Derived from N,N’-Di[(S)- -phenylethyl]cyclohexane-1,2-diamines in the Determination of the Optical Purity of Chiral Alcohols”, Tetrahedron: Asymmetry , 9, 2093-2099 (1998).

(4) I. Linzaga, J. Escalante, M. Muñoz y E. Juaristi, “NMR and X-Ray Crystallographic Studies of Axial and Equatorial 2-Ethoxy-2-oxo-1,4,2-oxazaphosphinane Derivatives”, Tetrahedron, 58, 8873 - 8978 (2002).

(5) G. Cuevas y E. Juaristi, “Manifestation of Stereoelectronic Effects on the Calculated Carbon-Hydrogen Bond Lengths and 1JC-H NMR Coupling Constants in Cyclohexane, Six-Membered Heterocycles, and Cyclohexanone Derivatives”, J. Am. Chem. Soc., 124, 13088-13096 (2002).

(6) I. Linzaga, J. Escalante, M. Muñoz y E. Juaristi, “NMR and X-Ray Crystallographic Studies of Axial and Equatorial 2-Ethoxy-2-oxo-1,4,2-oxazaphosphinane Derivatives”, Tetrahedron, 58, 8973-8978 (2002).

(7) G.E. Moreno, V.M. Mastranzo, L. Quintero, C. Anaya de Parrodi y E. Juaristi, “The Use of N,N’Di[a-Phenylethyl]ethane-1,2-diamines as Phosphorylated Chiral Derivatizing Agents for the Determination of the Enantiomeric Purity of Chiral Secondary Alcohols”, Rev. Soc. Quím. Méx., (Número especial dedicado a A. Romo de Vivar), 47, 127-129 (2003).

(8) A. Ariza Castolo, V. Bakhmutov, R. Contreras, N. Farfán, A. Flores, B. Gordillo, E. Juaristi, A. Paz, M.J. Rosales y R.L. Santillán, “Ejemplos Prácticos del Uso de la Resonancia Magnética Nuclear en la Química. Lecturas para Estudiantes”, Cinvestav-IPN: México (2006), ISBN: 968-9020-00-5.

(9) M. Hernández-Rodríguez y E. Juaristi, “Structurally Simple Chiral Thioureas as Chiral Solvating Agents in the Enantiodiscrimination of Carboxylic Acids”, Tetrahedron, 63, 7673-7678 (2007).

(10) G. Huelgas, S. Bernés, M. Sánchez, L. Quintero, E. Juaristi, C. Anaya de Parrodi y P. J. Walsh, “Synthesis and Dynamics of Atropisomeric (S)-N-(-Phenylelthyl)benzamides”, Tetrahedron, 63, 12655-12664 (2007).

(11) E. Juaristi y G. Cuevas, “Manifestations of Stereoelectronic Interactions in 1JC-H One Bond Coupling Constants”, Acc. Chem. Res., 40, 961-970 (2007).

Síntesis asimétrica

Pionero en México del desarrollo de la síntesis asimétrica. Publicaciones representativas:

(1) E. Juaristi, ed., “Enantioselective Synthesis of  -Amino Acids”, Wiley-VCH: New York, 1997,

(2) E. Juaristi y H. López-Ruiz, “Recent Advances in the Enantioselective Synthesis of  -Amino Acids”, Current Medicinal Chemistry, 6, 983-1004 (1999),

(3) E. Juaristi, J.L. León-Romo, A. Reyes y J. Escalante,“Recent Applications of -Phenylethylamine in the Preparation of Enantiopure Compounds”, Tetrahedron: Asymmetry , 10, 2441-2495 (1999).

(4) J.L. León-Romo, C.I. Virués, J. Aviña, I. Regla y E. Juaristi, “Preparation of (R)- and (S)--Methyldopa from a Chiral Hydantoin Containing the a-Phenethyl Group”, Chirality, 14, 144-150 (2002).

(5) V.M. Gutiérrez-García, G. Reyes-Ragel, O. Muñoz-Muñiz y E. Juaristi, “Enantioselective Síntesis of   -Amino Acids. Part 13. Diastereoselective Alkylation of Dianions Derived from Chiral Analogs of -Aminopropionic Acid Containing the -Phenylethyl Group”, Helv. Chim. Acta, 85, 4189-4199 (2002).

(6) O. Muñoz-Muñiz y E. Juaristi, “An Enantioselective Approach to the Biginelli Dihydropyridinone Condensation Reaction Using CeCl3 in the Presence of Chiral Ligands”, Arkivoc, 2003 (xi), 16-26 (2003). (Número Especial dedicado a la Química Orgánica en México).

(7) V.M. Mastranzo, L. Quintero, C. Anaya de Parrodi, E. Juaristi y P.J. Walsh, “Use of Diamines Containing the -Phenethyl Group as Chiral Ligands in the Asymmetric Hydrosilylation of Prochiral Ketones”, Tetrahedron, 60, 1781-1789 (2004).

(8)E. Castellanos, G. Reyes-Rangel y E. Juaristi, “Diastereoselective Electrophilic Amination of Chiral 1-Benzoyl-2-isopropyl-3-methyl-perhydropyrimidin-4-one in the Asymmetric Synthesis of -Substituted ,-Diaminopropionic Acid”, Helv. Chim. Acta , 87, 1016-1024 (2004).

(9)E. Juaristi y J. Aviña, “Diastereoselective Alkylation of Cyclo- -dipeptides en Route to Enantiopure -Amino Acids”, Pure and Appl. Chem. , 77, 1235-1241 (2005).

(10)C.G. Avila-Ortiz, G. Reyes-Rangel y E. Juaristi, “Enantioselective Synthesis of      -Amino Acids. 16. Preparation of Both Enantiomers to 2-(3,4-Dihydroxybenzyl)--alanine, Higher Homologues of Dopa”, Tetrahedron, 61, 8372-8381 (2005).

(11)E. Juaristi y V. Soloshonok, Eds., “Second Edition of Enantioselective Synthesis of -Amino Acids:”, Wiley: New York, ISBN: 0-471-46738-3 (2005).

(12) C. Anaya de Parrodi y E. Juaristi, “Chiral 1,2-Aminoalcohols and 1,2-Diamines Derived from Cyclohexene Oxide. Recent Applications in Asymmetric Synthesis”, Synlett, 2699-2715 (2006).

(13) G. Reyes-Rangel, V. Marañón, C.G. Avila-Ortiz, C. Anaya, L. Quintero y E. Juaristi, “Enantioselective Synthesis of (R)-2-Amino-3-phosphonopropionic Acid, (R)-AP-3, Via Diastereoselective Azidation of (4S,5R)-trans-N-[Diethoxyphosphoryl)-propionyl]hexahydrobenzoxazolidin-2-one”, Tetrahedron, 62, 8404-8409 (2006).

(14) V.M. Mastranzo, E. Santacruz, G. Huelgas, E. Paz, M.V. Sosa-Rivadeneyra, S. Bernes, E. Juaristi, L. Quintero y C. Anaya de Parrodi, “Synthesis of Novel Chiral Ligands Containing the N-(S)--Phenylethyl Group and Their Evaluation as Activators in the Enantioselective Addition of Et2Zn to Benzaldehyde”, Tetrahedron: Asymmetry, 17, 1663-1670 (2006).

(15) F. García-Flores, L. S. Flores-Michel y E. Juaristi, “Asymmetric Allylation of Benzoyl-hydrazones Promoted by Novel C2-Symmetric Bis-Sulfoxide Organocatalysts”, Tetrahedron Lett., 47, 8235-8238 (2006).

(16) Y. Liu, R. Melgar-Fernández y E. Juaristi, “Enantioselective Amination of -Phenyl -Cyanoacetate Catalyzed by Chiral Amines Incorporating the -Phenylethyl Auxiliary”, J. Org. Chem., 72, 1522-1525 (2007).

(17) R. Guzmán-Mejía, G. Reyes-Rangel y E. Juaristi, “Preparation of Chiral Derivatives of -Alanine Containing the -Phenylethyl Group: Useful Starting Materials for the Asymmetric Synthesis of -Amino Acids”, Nature Protocols, 2, 2759-2766 (2007).

(18) E. Juaristi, B.R.Díaz y J.L. Olivares,“Dioxa-, Oxathia- and Dithiazines”, en Comprehensive HeterocyclicChemistry III, Oxford, (2007); capítulo 9.10, pp.

(19) B.R. Díaz-Sánchez, M.A. Iglesias-Arteaga, R. Melgar-Fernández y E. Juaristi,“Synthesis of 2-Substituted-5-halo-2,3-dihydro-4(H)-pyrimidin-4-ones and Their Derivatization to Potential Precursors of -Substituted -Amino Acids Utilizing the Sonogashira Coupling Reaction”
J. Org. Chem., 72, 4822-4825 (2007).

(20) R. Melgar-Fernández, R. González-Olvera, J.L. Olivares-Romero, V. González-López, L. Romero-Ponce, M. Ramírez-Zárate, P. Demare, I. Regla y E. Juaristi “Synthesis of Novel Derivatives of (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane and their Evaluation as Potential Ligands in Asymmetric Catalysis”, Eur. J. Org. Chem., 655-672 (2008).

(21) R. González-Olvera, P. Demare, I. Regla y E. Juaristi,“Application of (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane Derivatives in Asymmetric Organocatlysis: the Biginelli Reaction”,
Arkivoc, Número Especial de Homenaje al Prof. Torbjorn Norin, vi, 61-72 (2008).

(22) M. Hernández-Rodríguez, C.G. Avila-Ortiz, J. Martín del Campo, D. Hernández-Romero, M.J. Rosales-Hoz y E. Juaristi, “Synthesis of Novel Chiral (Thio) Ureas and their Application as Organocatalysts in Asymmetric Synthesis”, Australian J. Chem., 61, 364-375 (2008).

(23) J.L. Olivares-Romero y E. Juaristi,“Synthesis of Two Novel Chiral Diamines Derived from (S)-Proline and their Evaluation as Precursors of Diazaborolidines for the Catalytic Borane-Mediated Enantioselective Reduction of Prochiral Ketones”, Tetrahedron, 64, 9992-9998 (2008).

(24) G. Reyes-Rangel, E. Jiménez-González, J.L. Olivares-Romero y E. Juaristi,“Enantioselective Synthesis of -Amino Acids Using Hexahydrobenzoxazolidi-nones as Chiral Auxiliaries”, Tetrahedron: Asymmetry, 2839 - 2849 (2008)

Síntesis de Compuestos con Actividad Biológica

Principalmente en el área de la síntesis enantioselectiva de - y -amino ácidos. Por ejemplo,

(1) el -amino--hidroxiácido 9-Bmt presente en el immunosupresor ciclosporina [D. Seebach, E. Juaristi, et al., Helv. Chim. Acta, 70, 237-261 (1987)],

(2) el ácido (S)-2-amino-fosfonopentanoico utilizado en pacientes con el mal de Alzheimer [O. García-Barradas y E. Juaristi, Tetrahedron, 51, 3423-3434 (1995)],

(3) la preparación del -hidroxi--amino ácido presente en el compuesto anticarcinogénico taxol [J. Escalante y E. Juaristi, Tetrahedron Lett. , 36, 4397-4400 (1995)],

(4) la síntesis enantioselectiva del (R)- y (S)-AP6, potentes agonistas del receptor AMPA [Tetrahedron Asymmetry, 8, 1511-1514 (1997)]

(5) la preparación de la (S)--metildopa, útil en el tratamiento del Parkinson [J.L. León-Romo, C.I. Virués, J. Aviña, I. Regla y E. Juaristi, Chirality, 14, 144 (2002)].

(6) R. Melgar-Fernández, P. Demare, E. Hong, J. Escalante, O. Muñoz-Muñiz, E. Juaristi y I. Regla, “Síntesis and Cardiovascular Activity of Metoprolol Analogs”, Bioorg. Med. Chem. Lett., 14, 191-194 (2004).

(7) G. Reyes-Rangel, V. Marañón, C.G. Avila-Ortiz, C. Anaya, L. Quintero y E. Juaristi, “Enantioselective Synthesis of (R)-2-Amino-3-phosphonopropionic Acid, (R)-AP-3, Via Diastereoselective Azidation of (4S,5R)-trans-N-[Diethoxyphosphoryl)-propionyl]hexahydrobenzoxazolidin-2-one”, Tetrahedron, 62, 8404-8409 (2006).

(8) P. Zubrzak, H. Williams, G.M. Coast, R.E. Isaac, G. Reyes-Rangel, E. Juaristi, J. Zabrocki y R.J. Nachman, “-Amino Acid Analogs of an Insect Neuropeptide Feature Potent Bioactivity and Resistance to Peptidase Hydrolysis”, Biopolymers: Peptide Science, 88, 76-82 (2007).

(9) E. Juaristi, “Retos para el Desarrollo de Fármacos en México”, en “Diseño y Producción de Fármacos”, E. Juaristi, Coordinador, El Colegio Nacional: en México (2007), capítulo 1, pp. 4-18.

(10) E. Juaristi, Coordinador, “Diseño y Producción de Fármacos”, El Colegio Nacional: México (2007). ISBN 978-970-640-356-8.

(11) S. Taneja-Bageshwar, A. Strey, P. Zubrzak, H. Williams, G. Reyes-Rangel, E. Juaristi, P. Pietrantonio y R.J. Nachman,“Identification of Selective and Non-Selective, Biostable -Amino Acid Agonists of Recombinant Insect Kinin Receptors from the Southern Cattle Tick Boophilus Microplus and Mosquito Aedes Aegypti”, Peptides, 29, 302-309 (2008).
 
Síntesis de péptidos no naturales
 Se ha consolidado un laboratorio de síntesis de péptidos. Algunas publicaciones representativas son:

(1) P. Zubrzak, H. Williams, G.M. Coast, R.E. Isaac, G. Reyes-Rangel, E. Juaristi, J. Zabrocki y R.J. Nachman, “-Amino Acid Analogs of an Insect Neuropeptide Feature Potent Bioactivity and Resistance to Peptidase Hydrolysis”, Biopolymers, Peptide Science, 88, 76-82 (2007).

(2) Y. Bandala, I.A. Rivero, T. González, J. Aviña, y E. Juaristi, “Solid Phase Synthesis of Novel /-Tetrapeptides and Electrospray Ionization Mass Spectrometric Evaluation of Their Metal Cation Complexation Behavior”, J. Phys. Org. Chem., 21, 349-358 (2008).

(3) S. Taneja-Bageshwar, A. Strey, P. Zubrzak, H. Williams, G. Reyes-Rangel, E. Juaristi, P. Pietrantonio y R.J. Nachman, “Identification of Selective and Non-Selective, Biostable -Amino Acid Agonists of Recombinant Insect Kinin Receptors from the Southern Cattle Tick Boophilus Microplus and Mosquito Aedes Aegypti”, Peptides, 29, 302-309 (2008).

(4) R.J. Nachman, O.B. Aziz, M. Davidovitch P. Zubrzak, R.E. Isaac, A. Strey, G. Reyes-Rangel, E. Juaristi, H.J.Williams y M. Altstein, “Biostable -Amino Acid PK/PBAN Analogs: Agonist and Antagonist Properties”, Peptides, 30, 608-615 (2009).
 
Síntesis Orgánica
Hemos desarrollado metodologías y reactivos de utilidad en síntesis orgánica; por ejemplo:

(1) E. Juaristi, “1-Benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one”, en Encyclopedia of Reagents for Organic Synthesis L.A. Paquette, ed., Wiley: Chichester, (2003); p. 53-56.

(2) J. Escalante, M.A. González-Tototzin, J. Aviña, O. Múñoz-Múñiz y E. Juaristi, “Synthesis of -Lactams and Cyclo--dipeptides from -Amino Acids”, Tetrahedron,57, 1883-1890 (2001).

(3) A. Reyes y E. Juaristi, “Convenient Route for the Preparation of C 2-Symmetric 2,3-Diphenylaziridine”, Chirality, 10, 95-99 (1998).

(4) C.A. de Parrodi, E. Juaristi, L. Quintero y A. Clara-Sosa, “A Useful Route to Enantiomerically Pure (4R,5R)- and (4R,5S)-N-(Propinoyl)-hexahydrobenzoxazolidin-2-ones”, Tetrahedron: Asymmetry, 8, 1075-1082 (1997).

(5)M.A. Iglesias-Arteaga, C. G. Avila-Ortiz y E. Juaristi, “Tandem Reactions Initiated by the Oxidative Decarboxylation of 1-Benzoyl-2(S)-tert-butyl-6( S)-carboxy-perhydropyridimidin-4-one”, Tetrahedron Lett., 43, 5297 (2002).

(6) M.A. Iglesias-Arteaga, E. Castellanos y E. Juaristi, “Alternative Procedure for the Synthesis of Enantiopure 1-Benzoyl-2(S)-tert-butyl-3-methylperhydropyrimidin-4-one, a Useful Starting Material for the Enantioselective Synthesis of -Substituted -Amino Acids”, Tetrahedron: Asymmetry, 14, 577-580 (2003).

(7) A.J. Mota, E. Castellano y E. Juaristi, “Simple Methodology for the Purification of Amino Acids”, Org. Prep. Proc. Int., 35, 414-417 (2003).

(8) V.M. Mastranzo, E. Santacruz, G. Huelgas, E. Paz, M.V. Sosa-Rivadeneyra, S. Bernes, E. Juaristi, L. Quintero y C. Anaya de Parrodi, “Synthesis of Novel Chiral Ligands Containing the N-(S)--Phenylethyl Group and Their Evaluation as Activators in the Enantioselective Addition of Et2Zn to Benzaldehyde”, Tetrahedron: Asymmetry, 17, 1663-1670 (2006).

(9) F. García-Flores, L. S. Flores-Michel y E. Juaristi, “Asymmetric Allylation of Benzoyl-hydrazones Promoted by Novel C2-Symmetric Bis-Sulfoxide Organocatalysts”, Tetrahedron Lett., 47, 8235-8238 (2006).

(10) E. Juaristi, O. Muñoz-Muñiz y R. Melgar-Fernández, “-Sodium Carboxylic Acids and Other Na-C-CXYZ Compounds (Including Sodium Enolates)”, en “Science of Synthesis”, Houben-Weyl Methods of Molecular Transformations, George Thieme Verlag, Stuttgart, (2006); chapter 8.2.15, pp. 1259-1284.
 
Diseño de organocatalizadores quirales

Pionero en México en la síntesis de nuevos organocatalizadores quirales, así como su aplicación en síntesis asimétrica. Algunas publicaciones representativas son:
 
(1) F. García-Flores, L.S. Flores-Michel y E. Juaristi, “Asymmetric Allylation of Benzoyl-hydrazones Promoted by Novel C2-Symmetric Bis-Sulfoxide Organocatalysts”, Tetrahedron Lett., 47, 8235-8238 (2006).

(2) Y. Liu, R. Melgar-Fernández y E. Juaristi, “Enantioselective Amination of -Phenyl -Cyanoacetate Catalyzed by Chiral Amines Incorporating the -Phenylethyl Auxiliary”, J. Org. Chem., 72, 1522-1525 (2007).

(3) R. González-Olvera, P. Demare, I. Regla y E. Juaristi, “Application of (1S,4S)-2,5-Diazabicyclo[2.2.1]heptane Derivatives in Asymmetric Organocatlysis: the Biginelli Reaction”, Arkivoc, Número Especial de Homenaje al Prof. Torbjorn Norin, vi, 61-72 (2008).

(4) M. Hernández-Rodríguez, C.G. Avila-Ortiz, J. Martín del Campo, D. Hernández-Romero, M.J. Rosales-Hoz y E. Juaristi, “Synthesis of Novel Chiral (Thio) Ureas and their Application as Organocatalysts in Asymmetric Synthesis”, Australian J. Chem., 61, 364-375 (2008).

(5) J.L. Olivares-Romero y E. Juaristi, “Synthesis of Two Novel Chiral Diamines Derived from (S)-Proline and their Evaluation as Precursors of Diazaborolidines for the Catalytic Borane-Mediated Enantioselective Reduction of Prochiral Ketones”, Tetrahedron, 64, 9992-9998 (2008).