Asymmetric synthesis of 2-arylpyrrolidines starting from gamma-chloro N-(tert-butanesulfinyl)ketimines

Erika Leemans; Sven Mangelinckx; Norbert De Kimpe

doi:10.1039/b925209f

Asymmetric synthesis of 2-arylpyrrolidines starting from gamma-chloro N-(tert-butanesulfinyl)ketimines

Chem Commun (Camb). 2010 May 14;46(18):3122-4. doi: 10.1039/b925209f. Epub 2010 Mar 31.

Authors

Erika Leemans¹, Sven Mangelinckx, Norbert De Kimpe

Affiliation

¹ Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.

PMID: 20358047
DOI: 10.1039/b925209f

Abstract

The enantioselective reductive cyclization of gamma-chloro N-(tert-butanesulfinyl)ketimines towards the short and efficient synthesis of (S)- and (R)-2-arylpyrrolidines (ee >99%) is described for the first time by treatment with LiBEt(3)H and subsequent acid deprotection.

Publication types

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

MeSH terms

Cyclization
Imines / chemical synthesis
Imines / chemistry*
Molecular Structure
Nitriles / chemical synthesis
Nitriles / chemistry*
Pyrrolidines / chemical synthesis
Pyrrolidines / chemistry*
Stereoisomerism

Substances

Imines
Nitriles
Pyrrolidines
ketimine