Enatioselective organocatalytic synthesis of highly functionalized tetrahydrothiophenes by a Michael-aldol cascade reaction

Guangshun Luo; Shilei Zhang; Wenhu Duan; Wei Wang

doi:10.1016/j.tetlet.2009.03.218

Enatioselective organocatalytic synthesis of highly functionalized tetrahydrothiophenes by a Michael-aldol cascade reaction

Guangshun Luo, Shilei Zhang, Wenhu Duan, Wei Wang

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

41 Scopus citations

Abstract

A catalytic asymmetric Michael-aldol cascade process for efficient synthesis of trisubstituted tetrahydrothiophenes is reported with high enantio- and diastereo-selectivities. Notably, three consecutive stereogenic centers including one chiral quaternary carbon center are efficiently created in the 'one-pot' operation.

Original language	English (US)
Pages (from-to)	2946-2948
Number of pages	3
Journal	Tetrahedron Letters
Volume	50
Issue number	24
DOIs	https://doi.org/10.1016/j.tetlet.2009.03.218
State	Published - Jun 17 2009
Externally published	Yes

Keywords

Cascade reactions
Michael-aldol
Organocatalysis
Tetrahydrothiophenes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2009.03.218

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@article{20947ef4e86e45089ab9c2f438ac12d7,

title = "Enatioselective organocatalytic synthesis of highly functionalized tetrahydrothiophenes by a Michael-aldol cascade reaction",

abstract = "A catalytic asymmetric Michael-aldol cascade process for efficient synthesis of trisubstituted tetrahydrothiophenes is reported with high enantio- and diastereo-selectivities. Notably, three consecutive stereogenic centers including one chiral quaternary carbon center are efficiently created in the 'one-pot' operation.",

keywords = "Cascade reactions, Michael-aldol, Organocatalysis, Tetrahydrothiophenes",

author = "Guangshun Luo and Shilei Zhang and Wenhu Duan and Wei Wang",

note = "Funding Information: We are grateful for the financial support from School of Pharmacy, East China University of Science and the National Science Foundation of China (Nos. 03772648 and 30721005), and the Chinese National Programs for High Technology Research and Development (Nos. 2006AA020602 and 2007AA02Z147). ",

year = "2009",

month = jun,

day = "17",

doi = "10.1016/j.tetlet.2009.03.218",

language = "English (US)",

volume = "50",

pages = "2946--2948",

journal = "Tetrahedron Letters",

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publisher = "Elsevier Limited",

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TY - JOUR

T1 - Enatioselective organocatalytic synthesis of highly functionalized tetrahydrothiophenes by a Michael-aldol cascade reaction

AU - Luo, Guangshun

AU - Zhang, Shilei

AU - Duan, Wenhu

AU - Wang, Wei

N1 - Funding Information: We are grateful for the financial support from School of Pharmacy, East China University of Science and the National Science Foundation of China (Nos. 03772648 and 30721005), and the Chinese National Programs for High Technology Research and Development (Nos. 2006AA020602 and 2007AA02Z147).

PY - 2009/6/17

Y1 - 2009/6/17

N2 - A catalytic asymmetric Michael-aldol cascade process for efficient synthesis of trisubstituted tetrahydrothiophenes is reported with high enantio- and diastereo-selectivities. Notably, three consecutive stereogenic centers including one chiral quaternary carbon center are efficiently created in the 'one-pot' operation.

AB - A catalytic asymmetric Michael-aldol cascade process for efficient synthesis of trisubstituted tetrahydrothiophenes is reported with high enantio- and diastereo-selectivities. Notably, three consecutive stereogenic centers including one chiral quaternary carbon center are efficiently created in the 'one-pot' operation.

KW - Cascade reactions

KW - Michael-aldol

KW - Organocatalysis

KW - Tetrahydrothiophenes

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DO - 10.1016/j.tetlet.2009.03.218

M3 - Article

AN - SCOPUS:65349183417

SN - 0040-4039

VL - 50

SP - 2946

EP - 2948

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 24

ER -

Enatioselective organocatalytic synthesis of highly functionalized tetrahydrothiophenes by a Michael-aldol cascade reaction

Abstract

Keywords

ASJC Scopus subject areas

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