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Organocatalytic Enantioselective Nucleophilic Alkynylation of Allyl Fluorides Affording Chiral Skipped Ene‐ynes
Author(s) -
Okusu Satoshi,
Okazaki Hiroki,
Tokunaga Etsuko,
Soloshonok Vadim A.,
Shibata Norio
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201601928
Subject(s) - enantioselective synthesis , allylic rearrangement , nucleophile , ene reaction , substrate (aquarium) , functional group , chemistry , catalysis , alkynylation , combinatorial chemistry , scope (computer science) , organic chemistry , computer science , oceanography , polymer , geology , programming language
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.