Organic Letters 2007-08-30

Enantioselective imidazole-directed allylation of aldimines and ketimines.

Nicholas R Perl, James L Leighton

Index: Org. Lett. 9 , 3699, (2007)

Full Text: HTML

Abstract

A new chiral allylchlorosilane has been developed that allows the highly enantioselective allylation and crotylation of a range of 2-imidazolylaldimines and ketimines. The method may be exploited for the protecting group-free synthesis of a diverse array of imidazole-bearing chiral carbinamines and, when coupled with ring-closing metathesis reactions, allows the one-pot synthesis of unusual heterocyclic motifs with potential relevance in medicinal chemistry.