Enantiodivergent Desymmetrization in the Rhodium( III)-Catalyzed Annulation of Sulfoximines with Diazo Compounds

被引：130

作者：

Shen, Bingxue ^{[1
,2
]}

Wan, Boshun ^{[1
]}

Li, Xingwei ^{[1
,3
]}

机构：

[1] Chinese Acad Sci, Dalian Inst Chem Phys, Dalian 116023, Peoples R China

[2] Univ Chinese Acad Sci, Beijing 100049, Peoples R China

[3] Shaanxi Normal Univ SNNU, Sch Chem & Chem Engn, Xian 710062, Shaanxi, Peoples R China

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2018年 / 57卷 / 47期

关键词：

asymmetric C-H activation; desymmetrization; enantiodivergence; rhodium; sulfoximes; C-H ACTIVATION; N BOND; ASYMMETRIC-SYNTHESIS; 2+2+2 CYCLOADDITION; FUNCTIONALIZATION; LIGANDS; COMBINATION; CATALYSIS; RH;

D O I：

10.1002/anie.201810472

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Rh-III- and Ir-III-catalyzed asymmetric C-H functionalization reactions of arenes have relied on the employment of chiral Rh-III/Ir-III cyclopentadienyl catalysts, the introduction of chiral carboxylic acids to achiral Cp*RhX2 catalysts, and the integration of both strategies. Despite considerable progress, each reaction only provided a specific configuration of the enantioenriched product when using a particular chiral catalyst. Reported in this work is the enantiodivergent coupling of sulfoximines with various diazo compounds by Rh-III-catalyzed desymmetrizing annulation. The enantiodivergence was enabled by a judicious choice of achiral carboxylic acids, and the enantioselectivity correlates with the steric bias of the carboxylic acid and the sulfoximine.

引用

页码：15534 / 15538

页数：5

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