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

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...

全面介紹

Saved in:

書目詳細資料
Main Authors:	Manat Pohmakotr, Duanghathai Panichakul, Patoomratana Tuchinda, Vichai Reutrakul
其他作者:	Mahidol University
格式:	Article
出版:	2018
主題:	Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics
在線閱讀:	https://repository.li.mahidol.ac.th/handle/123456789/24118
標簽:	添加標簽沒有標簽, 成為第一個標記此記錄!
機構:	Mahidol University

id	th-mahidol.24118
record_format	dspace
spelling	th-mahidol.241182018-08-24T09:14:13Z gem-Difluoromethylation of α- and γ-ketoesters: preparation of gem-difluorinated α-hydroxyesters and γ-butyrolactones Manat Pohmakotr Duanghathai Panichakul Patoomratana Tuchinda Vichai Reutrakul Mahidol University Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics 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. 2018-08-24T01:40:19Z 2018-08-24T01:40:19Z 2007-09-17 Article Tetrahedron. Vol.63, No.38 (2007), 9429-9436 10.1016/j.tet.2007.06.096 00404020 2-s2.0-34547612533 https://repository.li.mahidol.ac.th/handle/123456789/24118 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=34547612533&origin=inward
institution	Mahidol University
building	Mahidol University Library
continent	Asia
country	Thailand Thailand
content_provider	Mahidol University Library
collection	Mahidol University Institutional Repository
topic	Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics
spellingShingle	Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics Manat Pohmakotr Duanghathai Panichakul Patoomratana Tuchinda Vichai Reutrakul gem-Difluoromethylation of α- and γ-ketoesters: preparation of gem-difluorinated α-hydroxyesters and γ-butyrolactones
description	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.
author2	Mahidol University
author_facet	Mahidol University Manat Pohmakotr Duanghathai Panichakul Patoomratana Tuchinda Vichai Reutrakul
format	Article
author	Manat Pohmakotr Duanghathai Panichakul Patoomratana Tuchinda Vichai Reutrakul
author_sort	Manat Pohmakotr
title	gem-Difluoromethylation of α- and γ-ketoesters: preparation of gem-difluorinated α-hydroxyesters and γ-butyrolactones
title_short	gem-Difluoromethylation of α- and γ-ketoesters: preparation of gem-difluorinated α-hydroxyesters and γ-butyrolactones
title_full	gem-Difluoromethylation of α- and γ-ketoesters: preparation of gem-difluorinated α-hydroxyesters and γ-butyrolactones
title_fullStr	gem-Difluoromethylation of α- and γ-ketoesters: preparation of gem-difluorinated α-hydroxyesters and γ-butyrolactones
title_full_unstemmed	gem-Difluoromethylation of α- and γ-ketoesters: preparation of gem-difluorinated α-hydroxyesters and γ-butyrolactones
title_sort	gem-difluoromethylation of α- and γ-ketoesters: preparation of gem-difluorinated α-hydroxyesters and γ-butyrolactones
publishDate	2018
url	https://repository.li.mahidol.ac.th/handle/123456789/24118
_version_	1763492100626710528

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

相似書籍