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一种用于对映选择性合成α-和β-对称联萘酚的轴向手性喹啉-2-羧酸铜催化剂。

An Axially Chiral Quinoline-2-Carboxylic Acid-Cu Catalyst for Enantioselective Synthesis of - and -Symmetric BINOLs.

作者信息

Shen Ahui, Xu Jun, Gao Jun, Cen Shouyi, Zhang Zhipeng

机构信息

Key Laboratory for Advanced Materials and Joint International Research Laboratory of Precision Chemistry and Molecular Engineering, Feringa Nobel Prize Scientist Joint Research Center, Frontiers Science Center for Materiobiology and Dynamic Chemistry, School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai 200237, China.

School of Chemistry and Molecular Engineering, East China University of Science & Technology, Shanghai 200237, China.

出版信息

J Org Chem. 2024 Sep 6;89(17):12842-12847. doi: 10.1021/acs.joc.4c01421. Epub 2024 Aug 12.

Abstract

The in situ dimeric coordination of two chiral ligands bearing quinoline-2-carboxylic acid units and substituted BINOL backbones with a copper ion generates a new chiral catalyst for oxidative homo- and cross-coupling of various 2-naphthols, enabling enantioselective synthesis of a broad range of highly useful diversely substituted - and -symmetric BINOLs in up to 96% yield with good to excellent enantioselectivities (up to 98:2 e.r.).

摘要

带有喹啉 - 2 - 羧酸单元和取代联萘酚骨架的两个手性配体与铜离子的原位二聚配位作用生成了一种新型手性催化剂,用于各种2 - 萘酚的氧化均偶联和交叉偶联反应,能够对映选择性地合成多种高度有用的不同取代的对称联萘酚,产率高达96%,对映选择性良好至优异(高达98:2的对映体比例)。

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