Direct catalytic asymmetric mannich-type reactions of N-(2-hydroxyacetyl) pyrrole as an ester-equivalent donor

Abstract

(Chemical Equation Presented) Stretching the limits of the Mannich reaction: A new indium-binol catalyst was used to generate the enolate of the esterequivalent donor in situ (see scheme). The donor, an N-acyl pyrrole, has many similarities to an aromatic ketone, in particular the enolates should have the same coordination mode. Versatile β-amino-α-hydroxy carboxylic acid derivatives were obtained in high yield and ee values. © 2005 Wiley-VCH Verlag GmbH & Co. KGaA.