title: Acid-catalyzed cyclization of vinylsilanes bearing an amino group. Stereoselective synthesis of pyrrolidines
abstract: [reaction: see text] In the presence of an acid catalyst, vinylsilanes 1 bearing an amino group protected by an electron-withdrawing group were smoothly cyclized to 2-(silylmethyl)pyrrolidines 2. This cyclization was utilized for the stereoselective synthesis of 2,n-disubstituted pyrrolidines (n = 3-5). The cyclized products could be converted to the corresponding alcohols by oxidative cleavage of the carbon-silicon bond with TBAF and H2O2.
authors.affiliation: Department of Chemistry, University of Tsukuba, Ibaraki, Japan.
authors.initials: K
authors.lastname: Miura
authors.initials: T
authors.lastname: Hondo
authors.initials: T
authors.lastname: Nakagawa
authors.initials: T
authors.lastname: Takahashi
authors.initials: A
authors.lastname: Hosomi