title: Synthesis of stereodefined polysubstituted olefins. 1. Sequential intermolecular reactions involving selective, stepwise insertion of Pd(0) into allylic and vinylic halide bonds. The stereoselective synthesis of disubstituted olefins.
abstract: Palladium-catalyzed allylic substitution and cross-coupling reactions have been combined into a sequential procedure to provide a range of disubstituted olefin products starting from two-, three-, and four-carbon common olefin templates. Diverse application of this template strategy is demonstrated in a variety of model studies and in a parallel synthesis (combinatorial) approach to prepare an allylic amine molecular library. An approach toward the preparation of astaxanthin beta-D-diglucoside, an interesting antioxidant whose total synthesis has yet to be reported, using the olefin-template approach is also discussed.
authors.affiliation: Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, Canada M3J 1P3. organ@yorku.ca
authors.forename: M G
authors.initials: MG
authors.lastname: Organ
authors.forename: J T
authors.initials: JT
authors.lastname: Cooper
authors.forename: L R
authors.initials: LR
authors.lastname: Rogers
authors.forename: F
authors.initials: F
authors.lastname: Soleymanzadeh
authors.forename: T
authors.initials: T
authors.lastname: Paul
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis*; D010165:Palladium / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D000475:Alkenes; D010165:Palladium