期刊
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
卷 55, 期 51, 页码 15889-15893出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201609095
关键词
asymmetric catalysis; computational chemistry; lewis acids; organocatalysis; theoretical chemistry
资金
- National Science Foundation [CHE-1266022]
- Welch Foundation [A-1775]
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1266022] Funding Source: National Science Foundation
Computational analysis shows that the enantioselectivity of asymmetric Lewis-acid organocatalysis of the Diels-Alder cycloaddition of cyclopentadiene to cinnamates arises from stacking interactions that favor the addition of the diene to the more hindered face of the dienophile, while electrostatic interactions control the diastereoselectivity by selectively stabilizing the endo transition state. These results not only explain the stereoselectivity of these silylium-ion-ACDC reactions but should also guide the development of more effective ion-pairing asymmetric organocatalysts.
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