Journal
ORGANIC LETTERS
Volume 14, Issue 13, Pages 3288-3291Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol301243f
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Funding
- National Science Foundation [CHE-1059084, CHE-1012979, OCI-1053575]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1012979, 1059084] Funding Source: National Science Foundation
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Density functional theory (DFT) calculations were performed to investigate the origins of enantioselectivity in benzotetramisole (BTM)-catalyzed dynamic kinetic resolution of azlactones. The transition states of the fast-reacting enantiomer are stabilized by electrostatic interactions between the amide carbonyl group and the acetate anion bound to the nucleophile. The chiral BTM catalyst confines the conformation of the a-carbon and the facial selectivity of the nucleophilic attack to promote such electrostatic attractions.
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