Cooperative Catalytic Reactions Using Organocatalysts and Transition-Metal Catalysts: Enantioselective Propargylic Alkylation of Propargylic Alcohols with Aldehydes


  • This work was supported by Grant-in-Aids for Scientific Research for Young Scientists (S) (No. 19675002) and for Scientific Research on Priority Areas (No. 18066003) from the Ministry of Education, Culture, Sports, Science and Technology (Japan). Y.N. thanks the Ube Industries LTD. M.I. acknowledges the Global COE program for Chemistry Innovation.


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Working together: The title reaction proceeds in the presence of a thiolate-bridged diruthenium complex (2) and a secondary amine (1) to give the corresponding propargylic alkylated products in excellent yields as a mixture of two diastereoisomers, each with high enantioselectivity. The two catalysts activate propargylic alcohols and aldehydes, respectively, and cooperatively promote the enantioselective reaction.