title: Preparation and Reaction Chemistry of Novel Silicon-Substituted 1,3-Dienes.
abstract: 2-Silicon-substituted 1,3-dienes containing non transferrable groups known to promote transmetallation were prepared by Grignard chemistry and enyne metathesis. These dienes participated in one pot metathesis/Diels-Alder reactions in regio- and diastereoselective fashions. Electron-rich alkenes showed the fastest rates in metathesis reactions, and ethylene, a commonly used metathesis promoter slowed enyne metathesis. 2-Pyridyldimethylsilyl and 2-thienyldimethylsilyl substituted Diels-Alder cycloadducts participated in cross-coupling chemistry and the 2-thienyldimethylsilyl substituted cycloadducts underwent cross-coupling under very mild reaction conditions.
authors.affiliation: Department of Chemistry, Wake Forest University, P. O. Box 7486, Winston-Salem, NC 27109, USA. pchoudhury@gru.edu.
authors.forename: Partha P
authors.initials: PP
authors.lastname: Choudhury
authors.affiliation: Department of Chemistry, Wake Forest University, P. O. Box 7486, Winston-Salem, NC 27109, USA. welker@wfu.edu.
authors.forename: Mark E
authors.initials: ME
authors.lastname: Welker
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D061565:Cycloaddition Reaction; D015394:Molecular Structure; D012825:Silicon / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D012825:Silicon
keywords: 1,3-dienes; Diels-Alder; cross coupling; enyne metathesis; organosilanes