3,5-Bis-(trifluoromethyl)phenyl sulfones in the synthesis of 3,5-disubstituted cyclopent-2-enones

Autor:	Armin Babrowski, Carmen Nájera, Diego A. Alonso, Montserrat Varea, Mónica Fuensanta
Jazyk:	angličtina
Rok vydání:	2007
Předmět:	Sulfonyl chemistry.chemical_classification lcsh:QD241-441 chemistry.chemical_compound Trifluoromethyl chemistry Nucleophile lcsh:Organic chemistry Organic Chemistry Epoxide Cyclopentene Organic chemistry Alkene epoxidation
Zdroj:	ARKIVOC, Vol 2007, Iss 5, Pp 243-262 (2007)
ISSN:	1551-7012 1551-7004
Popis:	Bis-(trifluoromethyl)phenyl sulfones (BTFP sulfones) 1a-e, easily synthesized from 3,5-bis- (trifluoromethyl)benzenethiol, react under PTC with (Z)-1,4-dichloro-2-butene to afford the cyclopentenyl sulfones 3, which suffer further diastereoselective alkene epoxidation with MCPBA giving BTFP sulfonyl cyclopentene oxides 5 and 6 in good yields. These epoxides are convenient precursors of 3,5-disubstituted cyclopent-2-enones, which are given after epoxide ring-opening with different nucleophiles and final successive oxidation-BTFP sulfinate elimination.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::82f007027936a17d24b5522aeb4998d2 https://www.arkat-usa.org/arkivoc-journal/browse-arkivoc/ark.5550190.0008.519 Zobrazit plný text záznamu