Publication:
Intramolecular acylation of α-sulfinyl carbanions with masked α,β-unsaturated esters: a general strategy to 5-alkylidene-2-cyclopentenones

Issued Date

2007-02-19

Resource Type

Article

ISSN

00404020

DOI

10.1016/j.tet.2006.12.036

Other identifier(s)

2-s2.0-33846238520

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Tetrahedron. Vol.63, No.8 (2007), 1806-1820

Suggested Citation

Manat Pohmakotr, Sirinporn Thamapipol, Patoomratana Tuchinda, Vichai Reutrakul Intramolecular acylation of α-sulfinyl carbanions with masked α,β-unsaturated esters: a general strategy to 5-alkylidene-2-cyclopentenones. Tetrahedron. Vol.63, No.8 (2007), 1806-1820. doi:10.1016/j.tet.2006.12.036 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/24246

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Title

Intramolecular acylation of α-sulfinyl carbanions with masked α,β-unsaturated esters: a general strategy to 5-alkylidene-2-cyclopentenones

Author(s)

Manat Pohmakotr
 Sirinporn Thamapipol
 Patoomratana Tuchinda
 Vichai Reutrakul

Other Contributor(s)

Mahidol University

Abstract

A general method for the preparation of 5-alkylidene-2-cyclopentenones and their 2-phenylsulfanyl substituted derivatives, involving the intramolecular acylation of α-sulfinyl carbanions with cyclopentadiene-α,β-unsaturated esters as the key reaction followed by flash vacuum pyrolysis, is described. The reactions start from readily available Diels-Alder adducts, synthons of α-carbanions of α,β-unsaturated esters. © 2006 Elsevier Ltd. All rights reserved.

Keyword(s)

Biochemistry, Genetics and Molecular Biology
 Chemistry
 Pharmacology, Toxicology and Pharmaceutics

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URI

https://repository.li.mahidol.ac.th/handle/20.500.14594/24246

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Scopus 2006-2010