Recent Applications of Vinyl Sulfones and Vinyl Sulfoxides in Asymmetric Synthesis

TLDR: In this article, the synthesis of castanospermine stereoisomers from ω-amino-γ-oxygenated-α and β-unsaturated sulfones with methylene active ketones is described.

Abstract: Herein we present some new synthetic applications based on the use of functionalized α,β-unsaturated sulfones and α,β-unsaturated sulfoxides. In particular, we have developed a stereodivergent approach to the synthesis of castanospermine stereoisomers from ω-amino-γ-oxygenated-α.β-unsaturated sulfones as well as a stereoselective synthesis of substituted dihydrofurans by Pd(0) catalyzed reaction of the carbonate derivatives of γ-oxygenated-α.β-unsaturated sulfones with methylene active ketones. Additionally, the use of the sulfinyl group as a novel chiral auxiliary in asymmetric Heck reactions is also described.