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.
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.
Organ
M G
MG
Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, Canada M3J 1P3. organ@yorku.ca
Cooper
J T
JT
Rogers
L R
LR
Soleymanzadeh
F
F
Paul
T
T
D000475:Alkenes / Q000138:chemical synthesis*; D010165:Palladium / Q000494:pharmacology*; D013237:Stereoisomerism
D000475:Alkenes; D010165:Palladium