Organocatalytic asymmetric conjugate addition of thioacetic acid to β-nitrostyrenes

Hao Li; Jian Wang; Liansuo Zu; Wei Wang

doi:10.1016/j.tetlet.2006.02.036

Organocatalytic asymmetric conjugate addition of thioacetic acid to β-nitrostyrenes

Hao Li
, Jian Wang
, Liansuo Zu
, Wei Wang

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

80 Scopus citations

Abstract

A method for organocatalytic, enantioselective Michael addition reactions of thioacetic acid with a range of trans-β-nitrostyrenes has been developed. The processes, promoted by the chiral amine thiourea organocatalyst, take place in high yields with up to 70% ee.

Original language	English (US)
Pages (from-to)	2585-2589
Number of pages	5
Journal	Tetrahedron Letters
Volume	47
Issue number	15
DOIs	https://doi.org/10.1016/j.tetlet.2006.02.036
State	Published - Apr 10 2006
Externally published	Yes

Keywords

Amine thiourea
Asymmetric organocatalysis
Michael addition reaction
Nitroolefins
Thioacetic acid

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2006.02.036

Cite this

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title = "Organocatalytic asymmetric conjugate addition of thioacetic acid to β-nitrostyrenes",

abstract = "A method for organocatalytic, enantioselective Michael addition reactions of thioacetic acid with a range of trans-β-nitrostyrenes has been developed. The processes, promoted by the chiral amine thiourea organocatalyst, take place in high yields with up to 70\% ee.",

keywords = "Amine thiourea, Asymmetric organocatalysis, Michael addition reaction, Nitroolefins, Thioacetic acid",

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

note = "Funding Information: The financial support by the Department of Chemistry and the Research Allocation Committee, University of New Mexico is gratefully acknowledged. The Bruker X8 X-ray diffractometer was purchased via an NSF CRIF:MU award to the University of New Mexico, CHE-0443580. The expert X-ray crystallographic measurements made by Dr. Eileen N. Duesler are greatly appreciated. We thank Professor Cary Morrow for his comments about the manuscript. ",

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doi = "10.1016/j.tetlet.2006.02.036",

language = "English (US)",

volume = "47",

pages = "2585--2589",

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TY - JOUR

T1 - Organocatalytic asymmetric conjugate addition of thioacetic acid to β-nitrostyrenes

AU - Li, Hao

AU - Wang, Jian

AU - Zu, Liansuo

AU - Wang, Wei

N1 - Funding Information: The financial support by the Department of Chemistry and the Research Allocation Committee, University of New Mexico is gratefully acknowledged. The Bruker X8 X-ray diffractometer was purchased via an NSF CRIF:MU award to the University of New Mexico, CHE-0443580. The expert X-ray crystallographic measurements made by Dr. Eileen N. Duesler are greatly appreciated. We thank Professor Cary Morrow for his comments about the manuscript.

PY - 2006/4/10

Y1 - 2006/4/10

N2 - A method for organocatalytic, enantioselective Michael addition reactions of thioacetic acid with a range of trans-β-nitrostyrenes has been developed. The processes, promoted by the chiral amine thiourea organocatalyst, take place in high yields with up to 70% ee.

AB - A method for organocatalytic, enantioselective Michael addition reactions of thioacetic acid with a range of trans-β-nitrostyrenes has been developed. The processes, promoted by the chiral amine thiourea organocatalyst, take place in high yields with up to 70% ee.

KW - Amine thiourea

KW - Asymmetric organocatalysis

KW - Michael addition reaction

KW - Nitroolefins

KW - Thioacetic acid

UR - https://www.scopus.com/pages/publications/33644907743

UR - https://www.scopus.com/pages/publications/33644907743#tab=citedBy

U2 - 10.1016/j.tetlet.2006.02.036

DO - 10.1016/j.tetlet.2006.02.036

M3 - Article

AN - SCOPUS:33644907743

SN - 0040-4039

VL - 47

SP - 2585

EP - 2589

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

Organocatalytic asymmetric conjugate addition of thioacetic acid to β-nitrostyrenes

Abstract

Keywords

ASJC Scopus subject areas

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