Highly effective asymmetric hydrogenation of cyclic N-alkyl imines with chiral cationic Ru-MsDPEN catalysts

Fei Chen; Ziyuan Ding; Jie Qin; Tianli Wang; Yanmei He; Qing-Hua Fan

doi:10.1021/ol201679f

Highly effective asymmetric hydrogenation of cyclic N-alkyl imines with chiral cationic Ru-MsDPEN catalysts

Org Lett. 2011 Aug 19;13(16):4348-51. doi: 10.1021/ol201679f. Epub 2011 Jul 18.

Authors

Fei Chen¹, Ziyuan Ding, Jie Qin, Tianli Wang, Yanmei He, Qing-Hua Fan

Affiliation

¹ Beijing National Laboratory for Molecular Sciences, Institute of Chemistry and Graduate School, Chinese Academy of Sciences (CAS), Beijing 100190, PR China.

PMID: 21766831
DOI: 10.1021/ol201679f

Abstract

A range of cyclic N-alkyl imines were efficiently hydrogenated by using a chiral cationic Ru(η(6)-cymene)(MsDPEN)(BArF) complex (MsDPEN = N-(methanesulfonyl)-1,2-diphenylethylenediamine) in high yields and up to 98% ee. A one-pot synthesis of chiral 2-phenylpyrrolidine via reductive amination was also developed.

Publication types

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

MeSH terms

Amination
Catalysis
Cations / chemistry
Cyclization
Ethylenediamines / chemistry*
Hydrogenation
Imines / chemistry*
Molecular Structure
Oxidation-Reduction
Ruthenium / chemistry*
Stereoisomerism

Substances

Cations
Ethylenediamines
Imines
N-(methanesulfonyl)-1,2-diphenylethylenediamine
Ruthenium