ChemInform Abstract: Stereoselective Synthesis of (2E,4E)‐ and (2Z,4E)‐2,4‐Alkadienoates by the Ester Enolate Claisen Rearrangement of (E)‐1‐Alkyl‐3‐trimethylsilyl‐2‐propenyl Glycolates Followed by the Peterson Reaction.

Abstract

AbstractThe silylated propenyl glycolates (I), prepared from 2‐methyl‐1,3‐dioxolane‐4‐one and E‐1‐trimethylsilyl‐1‐alken‐3‐ols, are transformed into a mixture of threo‐ (II) and erythro‐hydroxytrimethylsilyl‐4‐alkenoates (III) by Claisen rearrangement, silylation of the intermediate dianion and subsequent methylation.