Tetrahedron Letters p. 5173 - 5176 (1997)
Update date:2022-08-04
Topics:
Ogura, Katsuyuki
Ogu, Ken-Ichi
Ayabe, Takashi
Sonehara, Jun-Ichi
Akazome, Motohiro
(E)-3-hydroxy-1-alkenyl p-tolyl sulfones (1) reacted with a hexafluoropropene-diethylamine adduct (PPDA) to afford α-fluoro-α-(trifluoromethyl)-β-[(p-tolylsulfonyl)methyl]-γ-lactones (2). This reaction is so stereoselective that only one diastereomer of 2 is detected in the reaction mixture. A plausible mechanism for this intriguing reaction is discussed.
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(1997)