Kissane, M,Murphy, M,Lawrence, SE,Maguire, AR;

2010

January

Tetrahedron: Asymmetry

Synthesis and stereoselective oxidation of alpha-thio-beta-chloropropenyloxazolidin-2-ones

Validated

WOS: 6 ()

THIO-BETA-CHLOROACRYLAMIDES ARYL BENZYL SULFOXIDES ASYMMETRIC-SYNTHESIS KINETIC RESOLUTION ALPHA-THIOAMIDES TRANSFORMATION AUXILIARIES

21

2550

2558

The investigation of the stereoselective reaction of alpha-thiopropanoyloxazolidin-2-ones with NCS to yield alpha-thio-beta-chloropropenyloxazolidin-2-ones is described Diastereoselective sulfur oxidation of the resulting alpha-thio-beta-chloropropenyloxazolidin-2-ones shows modest chastereocontrol However via a combination of diastereoselective oxidation and subsequent kinetic resolution in the sulfoxide oxidation diastereoselectivities of up to 94% de have been achieved (C) 2010 Elsevier Ltd All rights reserved

10.1016/j.tetasy.2010.10.007