Enantioselective hydrocyanation of N-protected aldimines

Masato Uemura; Nobuhito Kurono; Takeshi Ohkuma

doi:10.1021/ol203408w

Enantioselective hydrocyanation of N-protected aldimines

Org Lett. 2012 Feb 3;14(3):882-5. doi: 10.1021/ol203408w. Epub 2012 Jan 19.

Authors

Masato Uemura¹, Nobuhito Kurono, Takeshi Ohkuma

Affiliation

¹ Division of Chemical Process Engineering, Faculty of Engineering, Hokkaido University, Sapporo, Hokkaido 060-8628, Japan.

PMID: 22260419
DOI: 10.1021/ol203408w

Abstract

Enantioselective hydrocyanation of N-benzyloxycarbonyl aldimines catalyzed by a Ru[(S)-phgly](2)[(S)-binap]/C(6)H(5)OLi 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-C(4)H(9)OCH(3) with a substrate-to-catalyst molar ratio in the range of 500-5000 at -20 to 0 °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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Cyanates / chemistry*
Hydrogenation
Imines / chemistry*
Molecular Structure
Stereoisomerism

Substances

Cyanates
Imines