title: Computational evaluation of enantioselective Diels-Alder reactions mediated by Corey's cationic oxazaborolidine catalysts.
abstract: The cationic oxazaborolidine-catalyzed Diels-Alder reactions of butadiene and a series of five dienophiles have been studied using density functional theory (B3LYP/6-31G(d)). In each case, the computational results successfully reproduce the experimentally observed sense of stereoinduction and enantiomeric ratio. The computed structures of the lowest energy Lewis acid-carbonyl complexes and Lewis acid-transition state complexes are closely related to the models for stereoselection proposed by Corey and co-workers.
authors.affiliation: School of Chemistry, University of New South Wales, Sydney 2052, Australia. m.paddonrow@unsw.edu.au
authors.forename: Michael N
authors.initials: MN
authors.lastname: Paddon-Row
authors.forename: Christopher D
authors.initials: CD
authors.lastname: Anderson
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
mesh_terms: D000171:Acrolein / Q000031:analogs & derivatives / Q000737:chemistry; D000179:Acrylates / Q000737:chemistry; D016227:Benzoquinones / Q000737:chemistry; D001896:Boron Compounds / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002070:Butadienes / Q000737:chemistry; D003198:Computer Simulation; D000069462:Dimethyl Fumarate; D005650:Fumarates / Q000737:chemistry; D008958:Models, Molecular; D008968:Molecular Conformation; D013237:Stereoisomerism; D013379:Substrate Specificity
chemical_list: D000179:Acrylates; D016227:Benzoquinones; D001896:Boron Compounds; D019086:Bridged Bicyclo Compounds, Heterocyclic; D002070:Butadienes; D005650:Fumarates; C004532:quinone; D000171:Acrolein; C039175:methacrylaldehyde; D000069462:Dimethyl Fumarate; C035956:methyl acrylate