title: Enantioselective bromocycloetherification by Lewis base/chiral Brønsted 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.
authors.affiliation: Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana, Illinois 61801, USA. sdenmark@illinois.edu
authors.forename: Scott E
authors.initials: SE
authors.lastname: Denmark
authors.forename: Matthew T
authors.initials: MT
authors.lastname: Burk
mesh_terms: D000143:Acids / Q000737:chemistry*; D017605:Bromine Compounds / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D004986:Ether / Q000737:chemistry*; D058115:Lewis Bases / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000143:Acids; D017605:Bromine Compounds; D058115:Lewis Bases; D004986:Ether