Small Amounts of Achiral β-Amino Alcohols Reverse the Enantioselectivity of Chiral Catalysts in Cooperative Asymmetric Autocatalysis

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.