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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.

SUBMITTER: Paddon-Row MN

PROVIDER: S-EPMC2631179 | biostudies-literature | 2009 Jan

REPOSITORIES: biostudies-literature

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Computational evaluation of enantioselective Diels-Alder reactions mediated by Corey's cationic oxazaborolidine catalysts.

Paddon-Row Michael N MN Anderson Christopher D CD Houk K N KN

The Journal of organic chemistry 20090101 2

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 Co ...[more]

PMID: 19067584

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