Organocatalytic Enantioselective Nucleophilic Alkynylation of Allyl Fluorides Affording Chiral Skipped Ene‐ynes |
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| Authors: | Satoshi Okusu Hiroki Okazaki Etsuko Tokunaga Prof Vadim A Soloshonok Prof Norio Shibata |
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| Institution: | 1. Department of Nanopharmaceutical Sciences & Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, Japan;2. Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, San Sebastián, Spain;3. IKERBASQUE, Basque Foundation for Science, Bilbao, Spain |
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| Abstract: | Asymmetric methods for preparation of chiral alkynyl‐containing compounds are in extremely high demand in many sectors of chemical research. In this work, we report the discovery of a general organocatalytic enantioselective alkynylation based on the idea of Si/F activation of the allylic C?F bond. This approach features reasonably broad substrate scope, functional group tolerance, and relatively neutral, mild, and operationally convenient reaction conditions; all of which bode well for the synthetic value of the discovered method. In particular, this method provides unique chiral skipped 1,4‐ene‐ynes having two kinds of versatile functional groups. |
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| Keywords: | alkynes enantioselective fluorine organocatalysts silicon |
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