Issue 5, 2012
From the journal:

Chemical Science

Densely substituted unnatural l- and d-prolines as catalysts for highly enantioselective stereodivergent (3 + 2) cycloadditions and aldol reactions†

Egoitz Conde,a   Davide Bello,a   Abel de Cózar,a   Mirian Sánchez,a   Miguel A. Vázquezb  and  Fernando P. Cossío*a  

* Corresponding authors

a Departamento de Química Orgánica I, Universidad del País Vasco – Euskal Herriko Unibertsitatea and Donostia International Physics Center, Po Manuel de Lardizabal 3, 20018 San Sebastián-Donostia, Spain
E-mail: fp.cossio@ehu.es

b Departmento de Química, Universidad de Guanajuato Noria Alta s/n, 38050 Guanajuato, México

Abstract

(3 + 2) Cycloaddition reaction between azomethine ylides and π-deficient alkenes leads to densely substituted L- and D-unnatural prolines. These (3 + 2) cycloadducts in turn catalyse the preparation of an offspring of unnatural endo- and exo-L-proline derivatives. These latter compounds are also efficient catalysts of aldol reactions and yield aldol adducts with the opposite stereochemistry obtained under natural L-Pro organocatalysis.

Graphical abstract: Densely substituted unnatural l- and d-prolines as catalysts for highly enantioselective stereodivergent (3 + 2) cycloadditions and aldol reactions

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Article information

DOI
https://doi.org/10.1039/C2SC20199B
Article type
Edge Article
Submitted
17 Feb 2012
Accepted
21 Feb 2012
First published
22 Feb 2012

Chem. Sci., 2012,3, 1486-1491

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Densely substituted unnatural L- and D-prolines as catalysts for highly enantioselective stereodivergent (3 + 2) cycloadditions and aldol reactions

E. Conde, D. Bello, A. de Cózar, M. Sánchez, M. A. Vázquez and F. P. Cossío, Chem. Sci., 2012, 3, 1486 DOI: 10.1039/C2SC20199B

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