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

ABSTRACT: 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.

SUBMITTER: Wang C

PROVIDER: S-EPMC4526255 | biostudies-literature | 2015 Jul

REPOSITORIES: biostudies-literature

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

Wang Chuan C Yamamoto Hisashi H

Angewandte Chemie (International ed. in English) 20150608 30

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. ...[more]

PMID: 26058560

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