Reaction of 5-(trifluoromethyl)-2(5H)-furanone under basic conditions: Stereo-controlled Michael dimerization

Authors
Okano, T Chokai, M Eguchi, S Hayakawa, Y
Citation
T. Okano et al., Reaction of 5-(trifluoromethyl)-2(5H)-furanone under basic conditions: Stereo-controlled Michael dimerization, TETRAHEDRON, 56(34), 2000, pp. 6219-6222
Citations number
14
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
56
Issue
34
Year of publication
2000
Pages
6219 - 6222
Database
ISI
SICI code
0040-4020(20000818)56:34<6219:RO5UBC>2.0.ZU;2-E
Abstract
Treatment of 5-trifluoromethyl-2(5H)-furanone under basic conditions gave a stereoisomeric mixture of two out of four possible stereoisomers of bis(tr ifluoromethyl)dihydro-2,4-bisfuranonyl depending on the reaction conditions . Butenolide anion generated with LDA is kinetically stable and reaction wi th 2-cyclohexenone stereoselectively gave a Michael adduct. (C) 2000 Elsevi er Science Ltd. All rights reserved.