title: Intramolecular cycloaddition reactions of silyl nitronate tethered to vinylsilyl group: 2-nitroalkanols as precursors for amino polyols.
abstract: [reaction: see text] A method for converting 2-nitroalkanols to precursors for stereodefined amino polyols is described. Diphenylvinylsilylation of the 2-nitroalkanols' hydroxy groups and subsequent silyl nitronate generation by using TMS-Cl and Et(3)N in CH(3)CN at 0 degrees C to room temperature led to fused-bicyclic heterocycles through stereoselective intramolecular nitronate-olefin [3 + 2] cycloaddition reaction. Some examples for transforming the cycloadducts to amino polyols are also presented.
authors.affiliation: Department of Bioscience and Biotechnology, School of Engineering and School of Education, Okayama University, Tsushima, Okayama, Japan 700-8530.
authors.forename: Takayuki
authors.initials: T
authors.lastname: Kudoh
authors.forename: Teruhiko
authors.initials: T
authors.lastname: Ishikawa
authors.forename: Yoshihiro
authors.initials: Y
authors.lastname: Shimizu
authors.forename: Seiki
authors.initials: S
authors.lastname: Saito