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Enantioselective Bromocycloetherification by Lewis Base/Chiral Brønsted Acid Cooperative Catalysis

Author:
Denmark, Scott E., Burk, Matthew T.
Source:
Organic letters 2012 v.14 no.1 pp. 256-259
ISSN:
1523-7052
Subject:
Bronsted acids, Lewis bases, catalysts, catalytic activity, chemical bonding, chemical reactions, chemical structure, enantioselectivity, organic compounds
Abstract:
A binary catalyst system for the enantioselective bromocycloetherification of 5-arylpentenols is described. The combination of an achiral Lewis base and a chiral Brønsted acid affords good enantioselectivities for the cyclization of Z configured 5-arylpentenols to form bromomethyltetrahydrofurans. The constitutional site selectivity is highly dependent upon the aromatic substituent and the configuration of the double bond.
Agid:
5783727