title: Palladium-Catalyzed Markovnikov-Selective Hydroselenation of N-Vinyl Lactams with Selenols Affording N,Se-Acetals.
abstract: The highly regioselective hydroselenation of N-vinyl lactams has been revealed to successfully afford the corresponding N,Se-acetals as Markovnikov adducts. In the case of terminal N-vinyl lactams, Markovnikov-selective hydroselenation proceeds efficiently in the absence of any catalyst (or additive), owing to the acidity of the selenols. In contrast, the self-promoted hydroselenation is inefficient with internal N-vinyl lactams. In the presence of palladium diacetate (Pd(OAc)2), however, the desired hydroselenation of internal N-vinyl lactams proceeds efficiently to afford the corresponding N,Se-acetals.
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University , 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan.
authors.forename: Taichi
authors.initials: T
authors.lastname: Tamai
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University , 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan.
authors.forename: Megumi
authors.initials: M
authors.lastname: Yoshikawa
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University , 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan.
authors.forename: Shinya
authors.initials: S
authors.lastname: Higashimae
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University , 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan.
authors.forename: Akihiro
authors.initials: A
authors.lastname: Nomoto
authors.affiliation: Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University , 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan.
authors.forename: Akiya
authors.initials: A
authors.lastname: Ogawa