Synthesis of chiral β-amino acid derivatives by asymmetric hydrosilylation with an imidazole derived organocatalyst

The organocatalysed asymmetric hydrosilylation of a number of N-aryl and alkyl beta-substituted enamino esters proceeds in generally good yield and enantioselectivity. Crucial to obtaining high yield and selectivity was the addition of benzoic acid as an additive and under these conditions, both N-alkyl and N-aryl substituents were well tolerated. beta-Aryl and alkyl substituents were evaluated and a model proposed to account for the experimental observations based upon enamine tautomerisation and conformational preferences of the reactive ketimine intermediate. (c) 2012 Elsevier Ltd. All rights reserved.