Two complementary approaches toward 2-alkoxy carboxylic acid synthesis from 1,3-dioxolan-4-ones

Leonard L Winneroski; Yanping Xu

doi:10.1021/jo049784f

Two complementary approaches toward 2-alkoxy carboxylic acid synthesis from 1,3-dioxolan-4-ones

J Org Chem. 2004 Jul 23;69(15):4948-53. doi: 10.1021/jo049784f.

Authors

Leonard L Winneroski¹, Yanping Xu

Affiliation

¹ Lilly Research Laboratories, A Division of Eli Lilly and Company, Lilly Corporate Center, Indianapolis, IN 46285, USA.

PMID: 15255720
DOI: 10.1021/jo049784f

Abstract

Two complementary approaches to prepare 2-alkoxy carboxylic acids have been developed. Reductive ring opening of various 1,3-dioxolan-4-ones using TiCl(4)/Et(3)SiH or (t)BuMgCl affords the desired 2-alkoxy carboxylic acid in moderate to excellent chemical yield without loss of optical purity.