Catalytic enantioselective synthesis of flavanones and chromanones

Margaret M. Biddle; Michael Lin; Karl A. Scheidt

doi:10.1021/ja070394v

Catalytic enantioselective synthesis of flavanones and chromanones

Margaret M. Biddle, Michael Lin, Karl A. Scheidt^*

^*Corresponding author for this work

Chemistry

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

288 Scopus citations

Abstract

The enantioselective synthesis of flavanones and chromanones is described. Bifunctional thiourea catalysts promote an asymmetric oxo-conjugate addition to a β-ketoester alkylidene in high yields with excellent enantioselectivity (80-94% ee) for aryl and alkyl substrates. Decarboxylation of the β-ketoester proceeds smoothly in a one-pot procedure to afford the enantioenriched flavanones and chromanones.

Original language	English (US)
Pages (from-to)	3830-3831
Number of pages	2
Journal	Journal of the American Chemical Society
Volume	129
Issue number	13
DOIs	https://doi.org/10.1021/ja070394v
State	Published - Apr 4 2007

ASJC Scopus subject areas

Catalysis
General Chemistry
Biochemistry
Colloid and Surface Chemistry

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10.1021/ja070394v

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abstract = "The enantioselective synthesis of flavanones and chromanones is described. Bifunctional thiourea catalysts promote an asymmetric oxo-conjugate addition to a β-ketoester alkylidene in high yields with excellent enantioselectivity (80-94% ee) for aryl and alkyl substrates. Decarboxylation of the β-ketoester proceeds smoothly in a one-pot procedure to afford the enantioenriched flavanones and chromanones.",

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N2 - The enantioselective synthesis of flavanones and chromanones is described. Bifunctional thiourea catalysts promote an asymmetric oxo-conjugate addition to a β-ketoester alkylidene in high yields with excellent enantioselectivity (80-94% ee) for aryl and alkyl substrates. Decarboxylation of the β-ketoester proceeds smoothly in a one-pot procedure to afford the enantioenriched flavanones and chromanones.

AB - The enantioselective synthesis of flavanones and chromanones is described. Bifunctional thiourea catalysts promote an asymmetric oxo-conjugate addition to a β-ketoester alkylidene in high yields with excellent enantioselectivity (80-94% ee) for aryl and alkyl substrates. Decarboxylation of the β-ketoester proceeds smoothly in a one-pot procedure to afford the enantioenriched flavanones and chromanones.

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Catalytic enantioselective synthesis of flavanones and chromanones

Abstract

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CCDC 645761: Experimental Crystal Structure Determination

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Catalytic enantioselective synthesis of flavanones and chromanones

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 645761: Experimental Crystal Structure Determination

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