Polysusbtituted 1-hydroxycyclopentane carboxylic acid derivatives via a group-selective radical annulation

Abstract

A radical annulation procedure based on a highly stereoselective conjugated addition of a cyclic 1-hydroxyacid derivative to methyl acrylate followed by a fully group selective cyclization is reported. The 1,3-stereoinduction during the cyclization step is the only component of this process that is not fully controlled. The reaction furnished only two out of the 16 possible diastereomers. This reaction opens a new approach for the preparation of polysubstituted 1-hydroxycyclopentane carboxylic acid derivatives.