A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF<inf>3</inf>SiMe<inf>3</inf>as a trifluoromethylating agent

A general synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones is described. The fluoride-catalyzed nucleophilic addition of a trifluoromethyl (CF3) group generated from (trifluoromethyl)trimethylsilane (CF3SiMe3, Ruppert-Prakash reagent) to a masked maleic anhydride 1 (cyclopentadiene-ma...

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Main Authors:	Chonticha Masusai, Darunee Soorukram, Chutima Kuhakarn, Patoomratana Tuchinda, Chaveng Pakawatchai, Saowanit Saithong, Vichai Reutrakul, Manat Pohmakotr
Other Authors:	Mahidol University
Format:	Article
Published:	2018
Subjects:	Biochemistry, Genetics and Molecular Biology Chemistry
Online Access:	https://repository.li.mahidol.ac.th/handle/123456789/31190
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Institution:	Mahidol University

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spelling	th-mahidol.311902018-10-19T11:46:54Z A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF<inf>3</inf>SiMe<inf>3</inf>as a trifluoromethylating agent Chonticha Masusai Darunee Soorukram Chutima Kuhakarn Patoomratana Tuchinda Chaveng Pakawatchai Saowanit Saithong Vichai Reutrakul Manat Pohmakotr Mahidol University Prince of Songkla University Biochemistry, Genetics and Molecular Biology Chemistry A general synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones is described. The fluoride-catalyzed nucleophilic addition of a trifluoromethyl (CF3) group generated from (trifluoromethyl)trimethylsilane (CF3SiMe3, Ruppert-Prakash reagent) to a masked maleic anhydride 1 (cyclopentadiene-maleic anhydride adduct) provides the corresponding adducts 2 with high stereoselectivity. The γ-trifluoromethyl α,β-unsaturated γ-butyrolactones 4 were obtained after treatment of the adducts 2 with Grignard reagents, followed by flash-vacuum pyrolysis. © 2013 The Royal Society of Chemistry. 2018-10-19T04:35:13Z 2018-10-19T04:35:13Z 2013-10-14 Article Organic and Biomolecular Chemistry. Vol.11, No.38 (2013), 6650-6658 10.1039/c3ob41247d 14770520 2-s2.0-84884179676 https://repository.li.mahidol.ac.th/handle/123456789/31190 Mahidol University SCOPUS https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84884179676&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
spellingShingle	Biochemistry, Genetics and Molecular Biology Chemistry Chonticha Masusai Darunee Soorukram Chutima Kuhakarn Patoomratana Tuchinda Chaveng Pakawatchai Saowanit Saithong Vichai Reutrakul Manat Pohmakotr A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF<inf>3</inf>SiMe<inf>3</inf>as a trifluoromethylating agent
description	A general synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones is described. The fluoride-catalyzed nucleophilic addition of a trifluoromethyl (CF3) group generated from (trifluoromethyl)trimethylsilane (CF3SiMe3, Ruppert-Prakash reagent) to a masked maleic anhydride 1 (cyclopentadiene-maleic anhydride adduct) provides the corresponding adducts 2 with high stereoselectivity. The γ-trifluoromethyl α,β-unsaturated γ-butyrolactones 4 were obtained after treatment of the adducts 2 with Grignard reagents, followed by flash-vacuum pyrolysis. © 2013 The Royal Society of Chemistry.
author2	Mahidol University
author_facet	Mahidol University Chonticha Masusai Darunee Soorukram Chutima Kuhakarn Patoomratana Tuchinda Chaveng Pakawatchai Saowanit Saithong Vichai Reutrakul Manat Pohmakotr
format	Article
author	Chonticha Masusai Darunee Soorukram Chutima Kuhakarn Patoomratana Tuchinda Chaveng Pakawatchai Saowanit Saithong Vichai Reutrakul Manat Pohmakotr
author_sort	Chonticha Masusai
title	A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF<inf>3</inf>SiMe<inf>3</inf>as a trifluoromethylating agent
title_short	A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF<inf>3</inf>SiMe<inf>3</inf>as a trifluoromethylating agent
title_full	A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF<inf>3</inf>SiMe<inf>3</inf>as a trifluoromethylating agent
title_fullStr	A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF<inf>3</inf>SiMe<inf>3</inf>as a trifluoromethylating agent
title_full_unstemmed	A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF<inf>3</inf>SiMe<inf>3</inf>as a trifluoromethylating agent
title_sort	synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using cf<inf>3</inf>sime<inf>3</inf>as a trifluoromethylating agent
publishDate	2018
url	https://repository.li.mahidol.ac.th/handle/123456789/31190
_version_	1763491431319601152

A synthesis of γ-trifluoromethyl α,β-unsaturated γ-butyrolactones using CF<inf>3</inf>SiMe<inf>3</inf>as a trifluoromethylating agent

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