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

144 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

General Chemistry
Catalysis

Access to Document

10.1002/anie.201005908

Cite this

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

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.",

keywords = "Lewis acids, N-heterocyclic carbenes, asymmetric catalysis, asymmetric synthesis, homoenolates",

author = "Cohen, {Daniel T.} and Benoit Cardinal-David and Scheidt, {Karl A.}",

year = "2011",

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day = "11",

doi = "10.1002/anie.201005908",

language = "English (US)",

volume = "50",

pages = "1678--1682",

journal = "Angewandte Chemie - International Edition",

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publisher = "John Wiley and Sons Ltd",

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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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T1 - Lewis acid activated synthesis of highly substituted cyclopentanes by the n-heterocyclic carbene catalyzed addition of homoenolate equivalents to unsaturated ketoesters

AU - Cohen, Daniel T.

AU - Cardinal-David, Benoit

AU - Scheidt, Karl A.

PY - 2011/2/11

Y1 - 2011/2/11

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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DO - 10.1002/anie.201005908

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

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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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CCDC 793382: Experimental Crystal Structure Determination

CCDC 793381: Experimental Crystal Structure Determination

Cite this

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

Access to Document

Other files and links

Fingerprint

Datasets

CCDC 793382: Experimental Crystal Structure Determination

CCDC 793381: Experimental Crystal Structure Determination

Cite this