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Enantiodivergent Desymmetrization in the Rhodium(III)‐Catalyzed Annulation of Sulfoximines with Diazo Compounds
Author(s) -
Shen Bingxue,
Wan Boshun,
Li Xingwei
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201810472
Subject(s) - desymmetrization , diazo , chemistry , annulation , catalysis , enantioselective synthesis , rhodium , steric effects , cyclopentadienyl complex , organic chemistry , combinatorial chemistry , medicinal chemistry
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*RhX 2 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.