Enantioselective Hydrocyanation of N-Protected Aldimines

Overview

Title: 

Enantioselective Hydrocyanation of N-Protected Aldimines

Abstract: 

Enantioselective hydrocyanation of N-benzyloxycarbonyl aldimines catalyzed by a Ru[(S)-phgly](2)[(S)-binap]/C6H5OLi system or a bimetallic complex [Li{Ru[(S)-phgly](2)[(S)-binap]}]Cl affords the amino nitriles in 92-99% ee. The reaction is carried out in tert-C4H9OCH3 with a substrate-to-catalyst molar ratio in the range of 500-5000 at -20 to 0 degrees C. Primary, secondary, and tertiary alkyl imines as well as the aryl and heteroaryl substrates are smoothly cyanated to produce the desired products in high yield.

Authors: 

Masato Uemura, Nobuhito Kurono, Takeshi Ohkuma

DOI: 

Journal: 

Organic Letters

Year: 

2012

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