title: Chalcogeno-Morita-Baylis-Hillman reaction of enones with acetals: simple alpha-alkoxyalkylation of enones.
abstract: 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.
authors.affiliation: Gifu Pharmaceutical University, 6-1 Mitahora-higashi 5-chome, Gifu 502-8585, Japan.
authors.forename: Hironori
authors.initials: H
authors.lastname: Kinoshita
authors.forename: Takashi
authors.initials: T
authors.lastname: Osamura
authors.forename: Sayaka
authors.initials: S
authors.lastname: Kinoshita
authors.forename: Tatsunori
authors.initials: T
authors.lastname: Iwamura
authors.forename: Shin-Ichi
authors.initials: S
authors.lastname: Watanabe
authors.forename: Tadashi
authors.initials: T
authors.lastname: Kataoka
authors.forename: Genzoh
authors.initials: G
authors.lastname: Tanabe
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka