Enantioselective organocatalytic Michael additions of aldehydes to enones with imidazolidinones: Cocatalyst effects and evidence for an enamine intermediate

Timothy J. Peelen; Yonggui Chi; Samuel H. Gellman

doi:10.1021/ja0532584

Enantioselective organocatalytic Michael additions of aldehydes to enones with imidazolidinones: Cocatalyst effects and evidence for an enamine intermediate

Timothy J. Peelen, Yonggui Chi, Samuel H. Gellman^*

^*Corresponding author for this work

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

185 Citations (Scopus)

Abstract

An enantioselective intermolecular Michael addition of aldehydes to enones catalyzed by imidazolidinones has been achieved. Chemoselectivity (Michael addition vs aldol) can be controlled through judicious choice of hydrogen-bond-donating cocatalysts. The optimal imidazolidinone/hydrogen-bond-donor pair affords Michael addition products in excess of 90% ee. Furthermore, we have isolated and characterized an enamine intermediate and demonstrated its efficacy as a nucleophile in the observed Michael addition reactions.

Original language	English
Pages (from-to)	11598-11599
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	127
Issue number	33
DOIs	https://doi.org/10.1021/ja0532584
Publication status	Published - Aug 24 2005
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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abstract = "An enantioselective intermolecular Michael addition of aldehydes to enones catalyzed by imidazolidinones has been achieved. Chemoselectivity (Michael addition vs aldol) can be controlled through judicious choice of hydrogen-bond-donating cocatalysts. The optimal imidazolidinone/hydrogen-bond-donor pair affords Michael addition products in excess of 90% ee. Furthermore, we have isolated and characterized an enamine intermediate and demonstrated its efficacy as a nucleophile in the observed Michael addition reactions.",

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Enantioselective organocatalytic Michael additions of aldehydes to enones with imidazolidinones: Cocatalyst effects and evidence for an enamine intermediate. / Peelen, Timothy J.; Chi, Yonggui; Gellman, Samuel H.
In: Journal of the American Chemical Society, Vol. 127, No. 33, 24.08.2005, p. 11598-11599.

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

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AU - Peelen, Timothy J.

AU - Chi, Yonggui

AU - Gellman, Samuel H.

PY - 2005/8/24

Y1 - 2005/8/24

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AB - An enantioselective intermolecular Michael addition of aldehydes to enones catalyzed by imidazolidinones has been achieved. Chemoselectivity (Michael addition vs aldol) can be controlled through judicious choice of hydrogen-bond-donating cocatalysts. The optimal imidazolidinone/hydrogen-bond-donor pair affords Michael addition products in excess of 90% ee. Furthermore, we have isolated and characterized an enamine intermediate and demonstrated its efficacy as a nucleophile in the observed Michael addition reactions.

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Enantioselective organocatalytic Michael additions of aldehydes to enones with imidazolidinones: Cocatalyst effects and evidence for an enamine intermediate

Abstract

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