Article

 

Optimized Methodologies in Asymmetric Organic Synthesis Applying Microwaves^*

 

Yamir Bandala, Roberto Melgar–Fernández, Ramón Guzmán–Mejía, José Luis Olivares–Romero, Blanca Rosa Díaz–Sánchez, Rodrigo González–Olvera, Jorge Vargas–Caporali, and Eusebio Juaristi^*

 

Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado Postal 14–740, C.P. 07000, México, D. F. ^*Responsible author: ejuarist@cinvestav.mx, juaristi@relaq.mx.

 

Received July 13, 2009
Accepted September 17, 2009

 

Abstract

The use of microwave heating is a valuable tool for synthetic chemists. Being able to reduce reaction times and to increase product yield, this methodology offers to organic chemists the potential to optimize reaction processes. Additionally, microwave–assisted reactions provide more environmentally friendly reaction conditions. In this report, we describe results in the optimization of several organic reactions employed in the synthesis of various chiral molecules such as heterocycles, β–amino acids, and β–peptides, among others.

Keywords: Microwaves, Reaction Optimization, Organocatalysts, β–amino Acids, β–peptides.

 

Resumen

El uso de calentamiento por microondas es una valiosa herramienta para los químicos sintéticos. Esta metodología permite reducir los tiempos de reacción e incrementar el rendimiento de los productos, lo que equivale a optimizar los procesos de interés. Aunado a esto, las reacciones asistidas por microondas son más amigables al medio ambiente. En este trabajo se describen algunos resultados obtenidos en la optimización de varias reacciones orgánicas utilizadas para la síntesis de diversas moléculas quirales tales como heterociclos, β–aminoácidos y β–péptidos, entre otros.

Palabras Clave: Microondas, optimización de reacción, organocatalizadores, β–aminoácidos, β–péptidos.

 

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Acknowledgments

The authors are grateful to Consejo Nacional de Ciencia y Tecnología (CONACyT México) for financial support via grants 45157, and 60336. Y. Bandala, R. Melgar–Fernández, J.L. Olivares–Romero, B. Díaz–Sánchez, R. González–Olvera, and J. Vargas–Caporali are also indebted to CONACyT for their student fellowships.

 

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32. Crystal data for 19: C₂₂H₂₆N₂O₂, monoclinic, space group P 2(1), a = 10.9924(11)Å, b = 6.5469(19)Å, c = 13.2954(09)Å, α= γ= 90°, β= 96.4848(68)°, V = 950.6ų, crystal size: 0.3 × 0.2 × 0.1 mm³, R1 = 0.0441 (wR2 = 0.1087). Crystal data for 21: C₂₂H₂₆N₂S₂, monoclinic, space group P 2(1), a = 12.56660(50)Å, b = 6.03300(20)Å, c = 13.00150(59)Å, α= γ= 90°, β= 92.3405(15)°, V = 984.8776(68)ų, crystal size: 0.88 × 0.20 × 0.15 mm³, R1 = 0.0427 (wR2 = 0.1223). Crystal data for 29: C₂₃H₂₃NO₂, monoclinic, space group P 2(1), a = 9.8525(20)Å, b = 6.0365(12)Å, c = 16.2635(33)Å, α= γ= 90°, β= 104.788(30)°, V = 935.225ų, crystal size: 0.3 × 0.2 × 0.1 mm³, R1 = 0.0379 (wR2 = 0.0932). CCDC 740273 (19), CCDC 740274 (21), and CCDC 740275 (29) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Center via http://www.ccdc.cam.ac.uk/data_request/cif.

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Note

^*Dedicated to the memory of Ernest L. Eliel, caring mentor and friend.