Catalytic enantioselective conjugate alkynylation of β-Aryl-β-trifluoromethyl enones constructing propargylic all-carbon quaternary stereogenic centers

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2016
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American Chemical Society (ACS)
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Abstract
The enantioselective conjugate alkynylation of β-aryl-β-trifluoromethyl enones has been carried out using terminal alkynes and diethylzinc in the presence of 3,3′-bis-(perfluorophenyl)BINOL as the chiral ligand to give the corresponding ketones bearing a trifluoromethylated propargylic quaternary stereocenter with fair to good enantioselectivities. Enones bearing a bulky 2-naphthyl attached to the carbonyl group provided the best enantioselectivities. The synthetic applicability of the resulting products has been demonstrated with their iodocyclization to form 4H-pyrans.
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Sanz-Marco, A., Blay, G., Vila, C., & Pedro, J. R. (2016). Catalytic Enantioselective Conjugate Alkynylation of β-Aryl-β-trifluoromethyl Enones Constructing Propargylic All-Carbon Quaternary Stereogenic Centers. En Organic Letters (Vol. 18, Issue 15, pp. 3538-3541). American Chemical Society (ACS). https://doi.org/10.1021/acs.orglett.6b01494
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