Transition States of Vicinal Diamine-Catalyzed Aldol Reactions.

The transition states of aldol reactions catalyzed by vicinal diamines are characterized with density functional calculations. It was found that a cyclic transition state involving a nine-membered hydrogen-bonded ring is preferred. The crown (chair-chair) conformations of the transition state accoun...

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Detalles Bibliográficos
Publicado en:Journal of the American Chemical Society Vol. 138; no. 2; pp. 503 - 507
Autores principales: Simon, Adam, Yu-hong Lam, Houk, K. N.
Formato: Artículo
Publicado: American Chemical Society 1/20/2016
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Acceso en línea:Ver este registro en EBSCOhost
Descripción
Sumario:The transition states of aldol reactions catalyzed by vicinal diamines are characterized with density functional calculations. It was found that a cyclic transition state involving a nine-membered hydrogen-bonded ring is preferred. The crown (chair-chair) conformations of the transition state account for the observed stereoselectivity of these reactions.