One-pot, three-component synthesis of linearly substituted homoallylic alcohols via allyl(isopropoxy)dimethylsilane.
[reaction: see text] A two-step approach that involves the synthesis of vinylsilane from allyl(isopropoxy)dimethylsilane (6) and the subsequent Pd-catalyzed cross-coupling of the resulting vinylsilane is applied in developing a novel diversity-oriented, three-component synthesis to homoallylic alcohols of common structure 1. Upon treatment of 6 with s-BuLi, the silylallylmetal 5 is generated and reacted with carbonyl compounds to produce functionalized vinylsilanes, which can couple with aryl/vinyl halides in the presence of palladium catalyst to afford 1.
Department of Medicinal Chemistry, Merck Frosst Centre for Therapeutic Research, PO Box 1005, Pointe-Claire-Dorval, Quebec, Canada H9R 4P8.
Lianhai
L
Li
Neenah
N
Navasero
D000438:Alcohols / Q000138:chemical synthesis*; D000498:Allyl Compounds / Q000737:chemistry*; D002384:Catalysis; D007202:Indicators and Reagents; D015394:Molecular Structure; D012821:Silanes / Q000138:chemical synthesis*; D013237:Stereoisomerism; D014753:Vinyl Compounds / Q000138:chemical synthesis*
D000438:Alcohols; D000498:Allyl Compounds; D007202:Indicators and Reagents; D012821:Silanes; D014753:Vinyl Compounds; C476909:vinylsilane