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铑催化的未活化炔烃与 3-(硼酸化芳基)共轭烯酮的不对称环化反应:2,3-二取代茚的对映选择性合成。

Rhodium-Catalyzed Asymmetric Annulation of Unactivated Alkynes with 3-(-Boronated Aryl) Conjugated Enones: Enantioselective Synthesis of 2,3-Disubstituted Indenes.

机构信息

Institute of Material Physics & Chemistry, College of Science, Nanjing Forestry University, Nanjing 210037, P. R. China.

Co-Innovation Center for Sustainable Forestry in Southern China, Nanjing Forestry University, Nanjing 210037, P. R. China.

出版信息

J Org Chem. 2023 May 5;88(9):6140-6145. doi: 10.1021/acs.joc.2c02957. Epub 2023 Apr 5.

Abstract

A rhodium-catalyzed tandem arylation/cyclization reaction of 3-(ortho-boronated aryl) conjugated enones with unactivated alkynes is reported. By using a rhodium(I)/chiral-diene complex as the catalyst, the protocol was processed smoothly to provide various 2,3-disubstituted indene compounds in high yields with excellent regioselectivities and enantioselectivities. The approach outlined herein is appealing, as simple diarylalkynes, diakylalkynes, and alkyl(aryl)alkynes are the starting materials.

摘要

报道了铑催化的 3-(邻位硼芳基)共轭烯酮与未活化的炔烃的串联芳基化/环化反应。通过使用铑(I)/手性二烯配合物作为催化剂,该方法顺利进行,以高收率和优异的区域选择性和对映选择性提供了各种 2,3-二取代茚满化合物。本文所概述的方法很有吸引力,因为简单的二芳基炔、二烷基炔和芳基烷基炔都是起始原料。

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