Synthesis of enantiomerically enriched amino sulfide building blocks from acyclic chiral amino allylsilanes

J Org Chem. 2011 Sep 16;76(18):7415-22. doi: 10.1021/jo2010878. Epub 2011 Aug 18.

Abstract

An efficient synthesis of various protected syn-β-sulfenyl amides is described. These are prepared from the corresponding enantiopure amino allylsilanes which are in turn obtained from naturally occurring amino acids. The key step for introduction of the sulfur substituent is a diastereoselective electrophilic sulfodesilylation which is carried out with phthalimidesulfenyl chloride. The resulting homochiral β-phthalimidesulfenyl amines with an allylic sulforated stereogenic center are useful building blocks, as they represent a starting point for subsequent functional manipulations.