Gadolinium‐Catalyzed Regio‐ and Enantioselective Aminolysis of Aromatic  trans ‐2,3‐Epoxy Sulfonamides | Zendy

Wang Chuan | Zendy; Yamamoto Hisashi | Zendy

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Gadolinium‐Catalyzed Regio‐ and Enantioselective Aminolysis of Aromatic trans ‐2,3‐Epoxy Sulfonamides

Author(s) -

Wang Chuan,

Yamamoto Hisashi

Publication year - 2015

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.201503391

Subject(s) - aminolysis , enantioselective synthesis , sulfonamide , chemistry , moiety , catalysis , epoxy , ring (chemistry) , organic chemistry

The first enantioselective aminolysis of aromatic trans‐2,3‐epoxy sulfonamides has been accomplished, which was efficiently catalyzed by a Gd‐N,N′‐dioxide complex. Under the directing effect of the sulfonamide moiety the ring‐opening reaction proceeded selectively at the C‐3 position in a highly enantioselective manner furnishing various Ts‐ and SES‐protected 3‐amino‐3‐phenylpropan‐2‐olamines as products.

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