STEREOSELECTIVE FORMATION OF ALPHA-FLUORO-ALPHA-TRIFLUOROMETHYL-GAMMA-LACTONES STARTING FROM GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED SULFONES AND A HEXAFLUOROPROPENE-DIETHYLAMINE ADDUCT (PPDA)

Authors
OGURA K OGU K AYABE T SONEHARA J AKAZOME M
Citation
K. Ogura et al., STEREOSELECTIVE FORMATION OF ALPHA-FLUORO-ALPHA-TRIFLUOROMETHYL-GAMMA-LACTONES STARTING FROM GAMMA-HYDROXY-ALPHA,BETA-UNSATURATED SULFONES AND A HEXAFLUOROPROPENE-DIETHYLAMINE ADDUCT (PPDA), Tetrahedron letters, 38(29), 1997, pp. 5173-5176
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
38
Issue
29
Year of publication
1997
Pages
5173 - 5176
Database
ISI
SICI code
0040-4039(1997)38:29<5173:SFOA>2.0.ZU;2-H
Abstract
(E)-3-Hydroxy-1-alkenyl p-tolyl sulfones (1) reacted with a hexafluoro propen-diethylamine adduct (PPDA) to afford hyl)-beta-[(p-tolylsulfony l)methyl]-gamma-lactones (2). This reaction is so stereoselective that only one diastereomer of 2 is detected in the reaction mixture. A pla usible mechanism for this intriguing reaction is discussed. (C) 1997 E lsevier Science Ltd.