铜催化的芳基/杂芳基酮在温和水胶束条件下的不对称还原反应。

Copper-Catalyzed Asymmetric Reductions of Aryl/Heteroaryl Ketones under Mild Aqueous Micellar Conditions.

机构信息

Department of Chemistry & Biochemistry, University of California, Santa Barbara, California 93106, United States.

Anthem Biosciences Private Limited, Bommasandra Industrial Area, Phase-I, Bommasandra, Bangalore 560 099, India.

出版信息

Org Lett. 2021 May 7;23(9):3282-3286. doi: 10.1021/acs.orglett.1c00746. Epub 2021 Apr 27.

DOI:10.1021/acs.orglett.1c00746

PMID:33904740

Abstract

Enantioselective syntheses of nonracemic secondary alcohols have been achieved in an aqueous micellar medium via copper-catalyzed (Cu(OAc)·HO/()-3,4,5-MeO-MeO-BIPHEP) reduction of aryl/heteroaryl ketones. This methodology serves as a green protocol to access enantio-enriched alcohols under mild conditions (0-22 °C) using a base metal catalyst, together with an inexpensive, innocuous, and convenient stoichiometric hydride source (PMHS). The secondary alcohol products are formed in good to excellent yields with ee values greater than 90%.

摘要

通过铜催化（Cu(OAc)·HO/()-3,4,5-MeO-MeO-BIPHEP）还原芳基/杂芳基酮，在水胶束介质中实现了非外消旋仲醇的对映选择性合成。该方法是一种绿色的方法，在温和的条件（0-22°C）下使用廉价、无毒且方便的计量氢化试剂（PMHS），使用基础金属催化剂，获得对映体富集醇。仲醇产物的产率良好，ee 值大于 90%。