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手性联芳化合物的合成中,通过有机催化实现氧化芳构化反应时,轴向信息的反转。

Inversion of the Axial Information during Oxidative Aromatization in the Synthesis of Axially Chiral Biaryls with Organocatalysis as a Key Step.

机构信息

Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, 980-8578, Japan.

Frontier Research Center of Advanced Material and, Life Science Faculty of Advanced Life Science, Hokkaido University, Sapporo, 060-0810, Japan.

出版信息

Chemistry. 2020 Apr 6;26(20):4524-4530. doi: 10.1002/chem.201905814. Epub 2020 Feb 21.

Abstract

The pot-economical, highly enantioselective synthesis of axially chiral biaryls was developed by using one-pot organocatalyst-mediated domino and aromatization reactions as key steps. The axial information of the precursor, which also has central chirality, was completely inverted in the final biaryls. The inversion of the axial information occurred in the conversion of the central chirality to the axial chirality of an oxidative aromatization step.

摘要

一锅法有机催化的多步串联反应和芳构化反应为关键步骤,发展了一种经济、高对映选择性的轴手性联芳的合成方法。在最终的联芳产物中,前手性中心具有手性的轴手性完全反转。这种轴手性信息的反转发生在手性中心转化为氧化芳构化步骤的轴手性过程中。

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