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CuH 催化的 Bringmann 内酯的动态动力学拆分的对映选择性还原。

CuH-Catalyzed Atropoenantioselective Reduction of Bringmann's Lactones via Dynamic Kinetic Resolution.

机构信息

State Key Laboratory of Quality Research in Chinese Medicine, Institute of Chinese Medical Sciences , University of Macau , Macao , China.

Department of Chemistry , Southern University of Science and Technology , Shenzhen 518055 , China.

出版信息

Org Lett. 2019 Jul 19;21(14):5575-5580. doi: 10.1021/acs.orglett.9b01907. Epub 2019 Jun 27.

DOI:10.1021/acs.orglett.9b01907
PMID:31246482
Abstract

A CuH-catalyzed atropoenantioselective reduction of Bringmann's lactones via dynamic kinetic resolution has been disclosed. This protocol features a broad substrate scope and good functional group tolerance and allows the rapid assembly of various valuable axially chiral biaryls in good to high yields (up to 92% yield) with high to excellent enantioselectivities (up to 96% ee). Moreover, this report represents a rare example that a carbonyl group of esters is reduced under homogeneous asymmetric CuH catalysis.

摘要

一种通过动态动力学拆分实现的 CuH 催化的 Bringmann 内酯的非对映选择性还原被揭示。该方案具有广泛的底物范围和良好的官能团耐受性,并允许在高至优秀的对映选择性(高达 96%ee)下以良好至高收率(高达 92%收率)快速组装各种有价值的轴手性联苯。此外,该报告代表了在均相不对称 CuH 催化下酯的羰基被还原的罕见实例。

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