Chiral amine thiourea-promoted enantioselective domino Michael-aldol reactions between 2-mercaptobenzaldehydes and maleimides

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

doi:10.1002/adsc.200700158

Chiral amine thiourea-promoted enantioselective domino Michael-aldol reactions between 2-mercaptobenzaldehydes and maleimides

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

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

116 Scopus citations

Abstract

An organocatalytic, enantioselective domino Michael-aldol reaction of 2-mercaptobenz-aldehydes with maleimides has been developed. The process, catalyzed by a bifunctional chiral amine thiourea via a hydrogen-bonding mediated activation mechanism using as low as 1 mol % catalyst loading, affords versatile succinimide-containing benzothiopyrans with the generation of 3 stereogenic centers in one single operation.

Original language	English (US)
Pages (from-to)	1882-1886
Number of pages	5
Journal	Advanced Synthesis and Catalysis
Volume	349
Issue number	11-12
DOIs	https://doi.org/10.1002/adsc.200700158
State	Published - Aug 2007
Externally published	Yes

Keywords

Asymmetric catalysis
Asymmetric synthesis
Michael addition
Organic catalysis

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/adsc.200700158

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abstract = "An organocatalytic, enantioselective domino Michael-aldol reaction of 2-mercaptobenz-aldehydes with maleimides has been developed. The process, catalyzed by a bifunctional chiral amine thiourea via a hydrogen-bonding mediated activation mechanism using as low as 1 mol % catalyst loading, affords versatile succinimide-containing benzothiopyrans with the generation of 3 stereogenic centers in one single operation.",

keywords = "Asymmetric catalysis, Asymmetric synthesis, Michael addition, Organic catalysis",

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

year = "2007",

month = aug,

doi = "10.1002/adsc.200700158",

language = "English (US)",

volume = "349",

pages = "1882--1886",

journal = "Advanced Synthesis and Catalysis",

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AU - Zu, Liansuo

AU - Xie, Hexin

AU - Li, Hao

AU - Wang, Jian

AU - Jiang, Wei

AU - Wang, Wei

PY - 2007/8

Y1 - 2007/8

N2 - An organocatalytic, enantioselective domino Michael-aldol reaction of 2-mercaptobenz-aldehydes with maleimides has been developed. The process, catalyzed by a bifunctional chiral amine thiourea via a hydrogen-bonding mediated activation mechanism using as low as 1 mol % catalyst loading, affords versatile succinimide-containing benzothiopyrans with the generation of 3 stereogenic centers in one single operation.

AB - An organocatalytic, enantioselective domino Michael-aldol reaction of 2-mercaptobenz-aldehydes with maleimides has been developed. The process, catalyzed by a bifunctional chiral amine thiourea via a hydrogen-bonding mediated activation mechanism using as low as 1 mol % catalyst loading, affords versatile succinimide-containing benzothiopyrans with the generation of 3 stereogenic centers in one single operation.

KW - Asymmetric catalysis

KW - Asymmetric synthesis

KW - Michael addition

KW - Organic catalysis

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IS - 11-12

ER -

Chiral amine thiourea-promoted enantioselective domino Michael-aldol reactions between 2-mercaptobenzaldehydes and maleimides

Abstract

Keywords

ASJC Scopus subject areas

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