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.
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.
Ambhaikar
Narendra B
NB
Department of Chemistry, Emory University, Atlanta, Georgia 30322, USA.
Snyder
James P
JP
Liotta
Dennis C
DC