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铜催化的不对称分子内乌尔曼 C-N 偶联反应:吲哚啉的对映选择性制备。

Copper-catalyzed desymmetric intramolecular Ullmann C-N coupling: an enantioselective preparation of indolines.

机构信息

Key Laboratory of Regenerative Biology and Institute of Chemical Biology, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No. 190 Kaiyuan Avenue, Guangzhou Science Park, Guangzhou 510530, China.

出版信息

J Am Chem Soc. 2012 Sep 5;134(35):14326-9. doi: 10.1021/ja306631z. Epub 2012 Aug 24.

Abstract

The first highly enantioselective copper-catalyzed intramolecular Ullmann C-N coupling reaction has been developed. The asymmetric desymmetrization of 1,3-bis(2-iodoaryl)propan-2-amines catalyzed by CuI/(R)-BINOL-derived ligands led to the enantioselective formation of indolines in high yields and excellent enantiomeric excesses. This method was also applied to the formation of 1,2,3,4-tetrahydroquinolines in high yields and excellent enantioselectivity.

摘要

首次发展了高对映选择性的铜催化的内分子 Ullmann C-N 偶联反应。手性铜(I)/(R)-BINOL 衍生配体催化 1,3-双(2-碘芳基)丙-2-胺的不对称去对称化反应,以高产率和优异的对映选择性形成吲哚啉。该方法也适用于高产率和优异对映选择性的 1,2,3,4-四氢喹啉的形成。

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