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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.