BINAP/AgOTf/KF/18-crown-6 as new bifunctional catalysts for asymmetric Sakurai-Hosomi allylation and Mukaiyama aldol reaction |
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| Authors: | Wadamoto Manabu Ozasa Nobuko Yanagisawa Akira Yamamoto Hisashi |
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| Institution: | Graduate School of Engineering, Nagoya University, SORST, Japan Science and Technology Corporation (JST), Chikusa, Nagoya 464-8603, Japan. |
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| Abstract: | 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(I) 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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