Organocatalytic Enantioselective Nucleophilic Alkynylation of Allyl Fluorides Affording Chiral Skipped Ene-ynes.
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.
Department of Nanopharmaceutical Sciences & Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555, Japan.
Satoshi
S
Okusu
Department of Nanopharmaceutical Sciences & Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555, Japan.
Hiroki
H
Okazaki
Department of Nanopharmaceutical Sciences & Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555, Japan.
Etsuko
E
Tokunaga
Department of Organic Chemistry I, Faculty of Chemistry, University of the Basque Country UPV/EHU, 20018, San Sebastián, Spain.|IKERBASQUE, Basque Foundation for Science, Alameda Urquijo 36-5, Plaza Bizkaia, 48011, Bilbao, Spain.
Vadim A
VA
Soloshonok
Department of Nanopharmaceutical Sciences & Department of Frontier Materials, Nagoya Institute of Technology, Gokiso, Showa-ku, Nagoya, 466-8555, Japan. nozshiba@nitech.ac.jp.
Norio
N
Shibata
alkynes; enantioselective; fluorine; organocatalysts; silicon