Synthesis of highly functionalized chiral cyclopentanes by catalytic enantio- and diastereoselective double Michael addition reactions

Liansuo Zu; Hao Li; Hexin Xie; Jian Wang; Wei Jiang; Yun Tang; Wei Wang

doi:10.1002/anie.200700485

Synthesis of highly functionalized chiral cyclopentanes by catalytic enantio- and diastereoselective double Michael addition reactions

Liansuo Zu, Hao Li, Hexin Xie, Jian Wang, Wei Jiang, Yun Tang, Wei Wang

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

123 Scopus citations

Abstract

(Chemical Equation Presented) Do a double take: A novel highly enantio-and diastereoselective cascade double Michael reaction, in which two C-C bonds and three contiguous stereogenic centers are formed, has been developed. The one-pot process, which was efficiently catalyzed by the chiral diphenylprolinyl trimethylsilyl (TMS) ether, is a facile approach to synthetically useful chiral cyclopentanes (see scheme).

Original language	English (US)
Pages (from-to)	3732-3734
Number of pages	3
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	20
DOIs	https://doi.org/10.1002/anie.200700485
State	Published - 2007
Externally published	Yes

Keywords

Aldehydes
Cyclopentanes
Domino reactions
Michael addition
Organocatalysis

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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10.1002/anie.200700485

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title = "Synthesis of highly functionalized chiral cyclopentanes by catalytic enantio- and diastereoselective double Michael addition reactions",

abstract = "(Chemical Equation Presented) Do a double take: A novel highly enantio-and diastereoselective cascade double Michael reaction, in which two C-C bonds and three contiguous stereogenic centers are formed, has been developed. The one-pot process, which was efficiently catalyzed by the chiral diphenylprolinyl trimethylsilyl (TMS) ether, is a facile approach to synthetically useful chiral cyclopentanes (see scheme).",

keywords = "Aldehydes, Cyclopentanes, Domino reactions, Michael addition, Organocatalysis",

author = "Liansuo Zu and Hao Li and Hexin Xie and Jian Wang and Wei Jiang and Yun Tang and Wei Wang",

year = "2007",

doi = "10.1002/anie.200700485",

language = "English (US)",

volume = "46",

pages = "3732--3734",

journal = "Angewandte Chemie - International Edition",

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T1 - Synthesis of highly functionalized chiral cyclopentanes by catalytic enantio- and diastereoselective double Michael addition reactions

AU - Zu, Liansuo

AU - Li, Hao

AU - Xie, Hexin

AU - Wang, Jian

AU - Jiang, Wei

AU - Tang, Yun

AU - Wang, Wei

PY - 2007

Y1 - 2007

N2 - (Chemical Equation Presented) Do a double take: A novel highly enantio-and diastereoselective cascade double Michael reaction, in which two C-C bonds and three contiguous stereogenic centers are formed, has been developed. The one-pot process, which was efficiently catalyzed by the chiral diphenylprolinyl trimethylsilyl (TMS) ether, is a facile approach to synthetically useful chiral cyclopentanes (see scheme).

AB - (Chemical Equation Presented) Do a double take: A novel highly enantio-and diastereoselective cascade double Michael reaction, in which two C-C bonds and three contiguous stereogenic centers are formed, has been developed. The one-pot process, which was efficiently catalyzed by the chiral diphenylprolinyl trimethylsilyl (TMS) ether, is a facile approach to synthetically useful chiral cyclopentanes (see scheme).

KW - Aldehydes

KW - Cyclopentanes

KW - Domino reactions

KW - Michael addition

KW - Organocatalysis

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DO - 10.1002/anie.200700485

M3 - Article

C2 - 17431863

AN - SCOPUS:34250849026

SN - 1433-7851

VL - 46

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EP - 3734

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 20

ER -

Synthesis of highly functionalized chiral cyclopentanes by catalytic enantio- and diastereoselective double Michael addition reactions

Abstract

Keywords

ASJC Scopus subject areas

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