Phosphine-catalyzed enantioselective [3+2] annulations of 2,3-butadienoates with imines

The first systematic screening of chiral phosphines in the cycloaddition reaction between 2,3-butadienoates and arylimines has led to the identification of fairly efficient catalysts. 2-Aryl-3-pyrrolines have been obtained with enantiomeric excesses up to 64%. In one instance, the enantiomeric excess could be increased to 91% ee by combining the enantioselective cyclization reaction with a crystallization step. (c) 2006 Elsevier Ltd. All rights reserved.