Small amounts of achiral beta-amino alcohols reverse the enantioselectivity of chiral catalysts in cooperative asymmetric autocatalysis

François Lutz; Takashi Igarashi; Tsuneomi Kawasaki; Kenso Soai

doi:10.1021/ja054323c

Small amounts of achiral beta-amino alcohols reverse the enantioselectivity of chiral catalysts in cooperative asymmetric autocatalysis

J Am Chem Soc. 2005 Sep 7;127(35):12206-7. doi: 10.1021/ja054323c.

Authors

François Lutz¹, Takashi Igarashi, Tsuneomi Kawasaki, Kenso Soai

Affiliation

¹ Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka, Shinjuku-ku, Tokyo, 162-8601 Japan.

PMID: 16131182
DOI: 10.1021/ja054323c

Abstract

An asymmetric autocatalytic reaction has been catalyzed by a mixture of chiral and achiral beta-amino alcohols. The absolute configuration of the highly enantioenriched obtained product (>98% ee) was shown to depend not only on the absolute configuration of the chiral catalyst but also on the structure and the amount of achiral catalyst. Even in default versus the chiral catalyst, achiral catalysts were shown to be able to reverse the enantioselectivity of the reaction.