Diastereoselective addition of chlorotitanium enolate of N-acyl thiazolidinethione to O-methyl oximes: a novel, stereoselective synthesis of alpha,beta-disubstituted beta-amino carbonyl compounds via chiral auxiliary mediated azetine formation

Narendra B Ambhaikar; James P Snyder; Dennis C Liotta

doi:10.1021/ja029871u

Diastereoselective addition of chlorotitanium enolate of N-acyl thiazolidinethione to O-methyl oximes: a novel, stereoselective synthesis of alpha,beta-disubstituted beta-amino carbonyl compounds via chiral auxiliary mediated azetine formation

J Am Chem Soc. 2003 Apr 2;125(13):3690-1. doi: 10.1021/ja029871u.

Authors

Narendra B Ambhaikar¹, James P Snyder, Dennis C Liotta

Affiliation

¹ Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.

PMID: 12656586
DOI: 10.1021/ja029871u

Abstract

We have discovered a novel and highly diastereoselective synthesis of azetinyl thiazolidine-2-thiones that utilizes additions of the chlorotitanium enolates of N-acyl thiazolidin-2-thiones to O-methyl aldoximes. The "anti" azetines can be subsequently converted to the corresponding alpha,beta-disubstituted beta-amino carbonyl compound with retention of stereochemistry. The formation of azetine and the product of its "hydrolytic" opening has been confirmed by X-ray crystallographic analyses.