Chalcogeno-Morita-Baylis-Hillman reaction of enones with acetals: simple alpha-alkoxyalkylation of enones.
1-[2-(Methylsulfanyl)phenyl]prop-2-en-1-one (1) and the seleno congener (2) reacted with acetals 3 and 21 in the presence of BF(3).Et(2)O to give alpha-alkoxyalkyl enones 4, 5 and 22, 23 in good yields. When the reaction mixtures were worked up with a saturated NaHCO(3) solution instead of Et(3)N, onium salts 6 and 7 were obtained together with 4 and 5. Reactions with cyclic acetal 14 gave alpha-(beta-hydroxyethoxy) enones 15 and 16 accompanied by dimeric products 17 and 18.
Kinoshita
Hironori
H
Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan.
Osamura
Takashi
T
Kinoshita
Sayaka
S
Iwamura
Tatsunori
T
Watanabe
Shin-Ichi
S
Kataoka
Tadashi
T
Tanabe
Genzoh
G
Muraoka
Osamu
O