Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 68, Issue 14, Pages 5593-5601Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo020691c
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A catalytic amount of KF(.)18-crown-6 complex is effective as a soluble fluoride source to activate an asymmetric Sakurai-Hosomi allylation with BINAP and silver(l) triflate catalyst. The allylation of a variety of aromatic, alpha,beta-unsaturated and aliphatic aldehydes with allylic trimethoxysilane resulted in high yields and remarkable enantioselectivities. In addition, the asymmetric Mukaiyama-type aldol reaction is achieved by using trimethoxysilyl enol ethers in the presence of the same catalysts. High anti selectivity is obtained from E-silyl enol ether, while Z-silyl enol ether gives syn selectivity.
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