Catalytic Asymmetric Synthesis of Fluorine-containing Substrates (Flustrates)

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The purpose of this work is to develop the method for catalytic asymmetric synthesis of fluorine-containing substrates (flustrates) based on catalytic asymmetric carbonyl-ene, aldol, and Diels-Alder reactions with prochiral fluoral, difluoroacetaldehyde, and so forth. A summary of the research results is as follow :(1) Catalytic Asymmetric Ene Reaction with FluoralThe carbonyl-ene reaction with fluoral is found to afford the erythro-trifluoromethylcarbinol in more than 90% enantioselectivity by the asymmetric catalysis of chiral binaphthol-derived titanium complexes.(2) Catalytic Asymmetric Aldol Reaction with FluoralThe Mukaiyama aldol reaction with fluoral and difluoroacetaldehyde is found to afford the fluorine containing aldol products in more than 90% enantioselectivity by the asymmetric catalysis of chiral binaphthol-derived titanium complexes.(3) Catalytic Asymmetric Diels-Alder Reaction with FluoralThe asymmetric catalysis of Diels-Alder reaction with fluoral is so far unsuccessful even by the catalysis of chiral modified binaphthol-derived titanium complexes.