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Enantioselective bromocycloetherification by Lewis base/chiral Bronsted acid cooperative catalysis.

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.

SUBMITTER: Denmark SE

PROVIDER: S-EPMC3238797 | biostudies-literature | 2012 Jan

REPOSITORIES: biostudies-literature

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Enantioselective bromocycloetherification by Lewis base/chiral Brønsted acid cooperative catalysis.

Denmark Scott E SE Burk Matthew T MT

Organic letters 20111206 1

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. ...[more]

PMID: 22145621

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