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Origins of stereoselectivity in Diels-Alder cycloadditions catalyzed by chiral imidazolidinones.

ABSTRACT: B3LYP/6-31G(d) density functional theory has been used to study Diels-Alder reactions of cyclopentadiene with alpha,beta-unsaturated aldehydes and ketones organocatalyzed by MacMillan's chiral imidazolidinones. Preferred conformations of transition structures and reaction intermediates have been located. The dramatically different reactivities and enantioselectivities exhibited by two similar chiral imidazolidinones are rationalized.

SUBMITTER: Gordillo R

PROVIDER: S-EPMC3164120 | biostudies-literature | 2006 Mar

REPOSITORIES: biostudies-literature

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Origins of stereoselectivity in Diels-Alder cycloadditions catalyzed by chiral imidazolidinones.

Gordillo Ruth R Houk K N KN

Journal of the American Chemical Society 20060301 11

B3LYP/6-31G(d) density functional theory has been used to study Diels-Alder reactions of cyclopentadiene with alpha,beta-unsaturated aldehydes and ketones organocatalyzed by MacMillan's chiral imidazolidinones. Preferred conformations of transition structures and reaction intermediates have been located. The dramatically different reactivities and enantioselectivities exhibited by two similar chiral imidazolidinones are rationalized. ...[more]

PMID: 16536527

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