Enantioselective Bromocycloetherification by Lewis Base/Chiral Brønsted Acid Cooperative Catalysis

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. T...

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Bibliographic Details
Published in:Organic letters 2012-01, Vol.14 (1), p.256-259
Main Authors: Denmark, Scott E, Burk, Matthew T
Format: Article
Language:English
Subjects:
Acids - chemistry
Bromine Compounds - chemistry
Bronsted acids
Catalysis
catalysts
catalytic activity
chemical bonding
chemical reactions
chemical structure
Cyclization
enantioselectivity
Ether - chemistry
Lewis bases
Lewis Bases - chemistry
organic compounds
Stereoisomerism
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Summary: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.
ISSN:1523-7060
1523-7052
1523-7052
DOI:10.1021/ol203033k