Stereoselective approach to aminocyclopentitols from Garner aldehydes

Abstract

An efficient stereoselective synthesis of aminocyclopentitols from (S)- and (R)-Garner aldehydes is presented here. The key steps involved diastereoselective addition of vinylmagnesium bromide to a Garner aldehyde, ring closing metathesis, diastereoselective dihydroxylation and stereoselective reduction of the keto functionality.