Publication:
gem-Difluoromethylation of α- and γ-ketoesters: preparation of gem-difluorinated α-hydroxyesters and γ-butyrolactones

Issued Date

2007-09-17

Resource Type

Article

ISSN

00404020

DOI

10.1016/j.tet.2007.06.096

Other identifier(s)

2-s2.0-34547612533

Rights

Mahidol University

Rights Holder(s)

SCOPUS

Bibliographic Citation

Tetrahedron. Vol.63, No.38 (2007), 9429-9436

Suggested Citation

Manat Pohmakotr, Duanghathai Panichakul, Patoomratana Tuchinda, Vichai Reutrakul gem-Difluoromethylation of α- and γ-ketoesters: preparation of gem-difluorinated α-hydroxyesters and γ-butyrolactones. Tetrahedron. Vol.63, No.38 (2007), 9429-9436. doi:10.1016/j.tet.2007.06.096 Retrieved from: https://repository.li.mahidol.ac.th/handle/123456789/24118

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Title

gem-Difluoromethylation of α- and γ-ketoesters: preparation of gem-difluorinated α-hydroxyesters and γ-butyrolactones

Author(s)

Manat Pohmakotr
 Duanghathai Panichakul
 Patoomratana Tuchinda
 Vichai Reutrakul

Other Contributor(s)

Mahidol University

Abstract

PhSCF2SiMe3has been demonstrated as difluoromethyl carbanion synthon (-CF2H). It reacts chemoselectively with α- and γ-ketoesters at the keto group in the presence of a catalytic amount of TBAF in THF to give the corresponding α-hydroxy ester adducts as well as γ-gem-difluorophenylsulfanylmethylated-γ-butyrolactones in good yields. Reductive cleavage of the phenylsulfanyl group of these products employing Bu3SnH/AIBN gives the corresponding gem-difluoromethylated α-hydroxyesters and γ-butyrolactones in good yields. © 2007 Elsevier Ltd. All rights reserved.

Keyword(s)

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

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https://repository.li.mahidol.ac.th/handle/123456789/24118

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Scopus 2006-2010