Synthesis of chiral α-hydroxy acids via palladium-catalyzed C(sp(3))-H alkylation of lactic acid

Kai Chen; Xin Li; Shuo-Qing Zhang; Bing-Feng Shi

doi:10.1039/c5cc07879b

Synthesis of chiral α-hydroxy acids via palladium-catalyzed C(sp(3))-H alkylation of lactic acid

Chem Commun (Camb). 2016 Jan 31;52(9):1915-8. doi: 10.1039/c5cc07879b.

Authors

Kai Chen¹, Xin Li², Shuo-Qing Zhang², Bing-Feng Shi²

Affiliations

¹ Department of Chemistry, Zhejiang University, Hangzhou 310027, China. bfshi@zju.edu.cn and Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
² Department of Chemistry, Zhejiang University, Hangzhou 310027, China. bfshi@zju.edu.cn.

PMID: 26679740
DOI: 10.1039/c5cc07879b

Abstract

Herein we report a Pd-catalyzed alkylation of lactic acid with the assistance of 8-aminoquinoline auxiliary. A wide range of alkyl iodides bearing β-hydrogen atoms are compatible with the reaction conditions, providing a practical and straightforward alternative to access chiral α-hydroxy acids (AHAs). The new reactions have been applied for the synthesis of isotope-labeled AHAs and a sugar-containing complex AHA.

Publication types

Research Support, Non-U.S. Gov't