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

Ruth Gordillo, K. N. Houk

Research output: Contribution to journalArticle

111 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)3543-3553
Number of pages11
JournalJournal of the American Chemical Society
Volume128
Issue number11
DOIs
StatePublished - Mar 22 2006

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Cyclopentanes
Stereoselectivity
Reaction intermediates
Cycloaddition
Enantioselectivity
Cycloaddition Reaction
Ketones
Aldehydes
Density functional theory
Conformations

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Origins of stereoselectivity in Diels-Alder cycloadditions catalyzed by chiral imidazolidinones. / Gordillo, Ruth; Houk, K. N.

In: Journal of the American Chemical Society, Vol. 128, No. 11, 22.03.2006, p. 3543-3553.

Research output: Contribution to journalArticle

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