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Copper-Catalyzed Asymmetric Propargylic Substitution Reactions of Propargylic Acetates with Amines


  • 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). G.H. acknowledges the Global COE Program for Chemistry Innovation. Y.N. also thanks to the Iketani Science & Technology Foundation and the Japan Securities Scholarship Foundation. We thank Mr. Yusuke Shimada for some experiments at the initial stage of this work.


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Flexing your bipheps: Enantioselective propargylic substitution reactions of propargylic acetates with amines catalyzed by a copper-(R)-Cl-MeO-biphep or -binap complex give the corresponding propargylic amines in excellent yields with up to 89 % ee. The reaction described may provide a novel synthetic method for the preparation of chiral propargylic amines.

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