Organocatalytic enantioselective cascade michael-aldol condensation reactions: Efficient assembly of densely functionalized chiral cyclopentenes

Jian Wang; Hao Li; Hexin Xie; Liansuo Zu; Xu Shen; Wei Wang

doi:10.1002/anie.200703163

Organocatalytic enantioselective cascade michael-aldol condensation reactions: Efficient assembly of densely functionalized chiral cyclopentenes

Jian Wang, Hao Li, Hexin Xie, Liansuo Zu, Xu Shen, Wei Wang

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

93 Scopus citations

Abstract

(Chemical Equation Presented) A cascade of possibility: A novel and highly enantioselective cascade Michael-aldol condensation reaction of α,β-unsaturated aldehydes with dimethyl malonate aldehyde has been developed. The process, efficiently catalyzed by a simple chiral diphenylprolinol TES ether, serves as a powerful approach to the preparation of highly functionalized chiral cyclopentenes with the formation of two new C-C bonds. TES = triethylsilyl.

Original language	English (US)
Pages (from-to)	9050-9053
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	47
DOIs	https://doi.org/10.1002/anie.200703163
State	Published - 2007
Externally published	Yes

Keywords

Aldehydes
Cascade reactions
Cyclopentenes
Michael-aldol reaction
Organocatalysis

ASJC Scopus subject areas

Catalysis
General Chemistry

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10.1002/anie.200703163

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title = "Organocatalytic enantioselective cascade michael-aldol condensation reactions: Efficient assembly of densely functionalized chiral cyclopentenes",

abstract = "(Chemical Equation Presented) A cascade of possibility: A novel and highly enantioselective cascade Michael-aldol condensation reaction of α,β-unsaturated aldehydes with dimethyl malonate aldehyde has been developed. The process, efficiently catalyzed by a simple chiral diphenylprolinol TES ether, serves as a powerful approach to the preparation of highly functionalized chiral cyclopentenes with the formation of two new C-C bonds. TES = triethylsilyl.",

keywords = "Aldehydes, Cascade reactions, Cyclopentenes, Michael-aldol reaction, Organocatalysis",

author = "Jian Wang and Hao Li and Hexin Xie and Liansuo Zu and Xu Shen and Wei Wang",

year = "2007",

doi = "10.1002/anie.200703163",

language = "English (US)",

volume = "46",

pages = "9050--9053",

journal = "Angewandte Chemie - International Edition",

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publisher = "John Wiley and Sons Ltd",

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T1 - Organocatalytic enantioselective cascade michael-aldol condensation reactions

T2 - Efficient assembly of densely functionalized chiral cyclopentenes

AU - Wang, Jian

AU - Li, Hao

AU - Xie, Hexin

AU - Zu, Liansuo

AU - Shen, Xu

AU - Wang, Wei

PY - 2007

Y1 - 2007

N2 - (Chemical Equation Presented) A cascade of possibility: A novel and highly enantioselective cascade Michael-aldol condensation reaction of α,β-unsaturated aldehydes with dimethyl malonate aldehyde has been developed. The process, efficiently catalyzed by a simple chiral diphenylprolinol TES ether, serves as a powerful approach to the preparation of highly functionalized chiral cyclopentenes with the formation of two new C-C bonds. TES = triethylsilyl.

AB - (Chemical Equation Presented) A cascade of possibility: A novel and highly enantioselective cascade Michael-aldol condensation reaction of α,β-unsaturated aldehydes with dimethyl malonate aldehyde has been developed. The process, efficiently catalyzed by a simple chiral diphenylprolinol TES ether, serves as a powerful approach to the preparation of highly functionalized chiral cyclopentenes with the formation of two new C-C bonds. TES = triethylsilyl.

KW - Aldehydes

KW - Cascade reactions

KW - Cyclopentenes

KW - Michael-aldol reaction

KW - Organocatalysis

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DO - 10.1002/anie.200703163

M3 - Article

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SN - 1433-7851

VL - 46

SP - 9050

EP - 9053

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 47

ER -

Organocatalytic enantioselective cascade michael-aldol condensation reactions: Efficient assembly of densely functionalized chiral cyclopentenes

Abstract

Keywords

ASJC Scopus subject areas

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