Lewis acid activated synthesis of highly substituted cyclopentanes by the n-heterocyclic carbene catalyzed addition of homoenolate equivalents to unsaturated ketoesters

Daniel T. Cohen; Benoit Cardinal-David; Karl A. Scheidt

doi:10.1002/anie.201005908

Lewis acid activated synthesis of highly substituted cyclopentanes by the n-heterocyclic carbene catalyzed addition of homoenolate equivalents to unsaturated ketoesters

Daniel T. Cohen, Benoit Cardinal-David, Karl A. Scheidt

Chemistry

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

136 Scopus citations

Abstract

A great team: Cyclopentanes with four contiguous stereogenic centers were assembled with excellent diastereo- and enantioselectivity from simple β,γ-unsaturated α-ketoesters and enals in a reaction catalyzed by an N-heterocyclic carbene (NHC) and mediated by a titanium(IV) Lewis acid (see scheme). The presence of a Lewis acid was essential for the desired transformation to occur.

Original language	English (US)
Pages (from-to)	1678-1682
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	7
DOIs	https://doi.org/10.1002/anie.201005908
State	Published - Feb 11 2011

Keywords

Lewis acids
N-heterocyclic carbenes
asymmetric catalysis
asymmetric synthesis
homoenolates

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.201005908

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abstract = "A great team: Cyclopentanes with four contiguous stereogenic centers were assembled with excellent diastereo- and enantioselectivity from simple β,γ-unsaturated α-ketoesters and enals in a reaction catalyzed by an N-heterocyclic carbene (NHC) and mediated by a titanium(IV) Lewis acid (see scheme). The presence of a Lewis acid was essential for the desired transformation to occur.",

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Lewis acid activated synthesis of highly substituted cyclopentanes by the n-heterocyclic carbene catalyzed addition of homoenolate equivalents to unsaturated ketoesters. / Cohen, Daniel T.; Cardinal-David, Benoit; Scheidt, Karl A.

In: Angewandte Chemie - International Edition, Vol. 50, No. 7, 11.02.2011, p. 1678-1682.

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

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AU - Cardinal-David, Benoit

AU - Scheidt, Karl A.

PY - 2011/2/11

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N2 - A great team: Cyclopentanes with four contiguous stereogenic centers were assembled with excellent diastereo- and enantioselectivity from simple β,γ-unsaturated α-ketoesters and enals in a reaction catalyzed by an N-heterocyclic carbene (NHC) and mediated by a titanium(IV) Lewis acid (see scheme). The presence of a Lewis acid was essential for the desired transformation to occur.

AB - A great team: Cyclopentanes with four contiguous stereogenic centers were assembled with excellent diastereo- and enantioselectivity from simple β,γ-unsaturated α-ketoesters and enals in a reaction catalyzed by an N-heterocyclic carbene (NHC) and mediated by a titanium(IV) Lewis acid (see scheme). The presence of a Lewis acid was essential for the desired transformation to occur.

KW - Lewis acids

KW - N-heterocyclic carbenes

KW - asymmetric catalysis

KW - asymmetric synthesis

KW - homoenolates

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Lewis acid activated synthesis of highly substituted cyclopentanes by the n-heterocyclic carbene catalyzed addition of homoenolate equivalents to unsaturated ketoesters

Abstract

Keywords

ASJC Scopus subject areas

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