Preparation and Reactions of Optically Active 4-Hydroxy-1,3-dioxolanes: 2-Hydroxy Aldehyde Equivalents

Abstract

The preparation and reactions of optically and chemically stable (S)-4-hydroxy-1,3-dioxolane 3 as a 2-hydroxy aldehyde equivalent were explored. Hydroxydioxolane 3 was prepared by reduction of ketodioxolane 2 which was obtained from (S)-2-hydroxycarboxylic acid 1. The reactions of 3 with triethyl phosphonoacetate and organometallic reagents were carried out. These and other conversions gave synthetically and biologically useful products in moderate to good chemical and moderate stereochemical yields.