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

Ruth Gordillo; K. N. Houk

doi:10.1021/ja0525859

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

Ruth Gordillo, K. N. Houk

Research output: Contribution to journal › Article › peer-review

129 Scopus citations

Abstract

B3LYP/6-31G(d) density functional theory has been used to study Diels-Alder reactions of cyclopentadiene with α,β-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.

Original language	English (US)
Pages (from-to)	3543-3553
Number of pages	11
Journal	Journal of the American Chemical Society
Volume	128
Issue number	11
DOIs	https://doi.org/10.1021/ja0525859
State	Published - Mar 22 2006

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Biochemistry
Colloid and Surface Chemistry

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abstract = "B3LYP/6-31G(d) density functional theory has been used to study Diels-Alder reactions of cyclopentadiene with α,β-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.",

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AB - B3LYP/6-31G(d) density functional theory has been used to study Diels-Alder reactions of cyclopentadiene with α,β-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.

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

Abstract

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