Highly enantioselective copper(I)-catalyzed conjugate addition of terminal alkynes to 1,1-difluoro-1-(phenylsulfonyl)-3-en-2-ones: new ester/amide surrogates in asymmetric catalysis

Chemistry : a European Journal
Amparo Sanz-MarcoJosé R Pedro

Abstract

A highly enantioselective copper-catalyzed conjugate alkynylation of monoactivated enones, namely 1,1-difluoro-1-(phenylsulfonyl)-3-en-2-ones, is described. The reaction products are obtained with good yields and excellent enantioselectivities (from 92 to 99% ee). The β-alkynylated difluoro(phenylsulfonyl) ketones can be converted into the corresponding β-alkynylated difluoro- and trifluoromethyl ketones, esters and amides. This is the first example on the use of 1,1-difluoro-1-(phenylsulfonyl)-3-en-2-ones as substrates in an enantioselective reaction, which have been shown to be new ester/amide surrogates.

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Citations

Feb 3, 2015·Chemistry : a European Journal·David MongeYolanda Alvarez-Casao
Jul 18, 2020·Chemical Communications : Chem Comm·Gonzalo BlayJosé R Pedro
Aug 20, 2020·Chemical Communications : Chem Comm·Fu-Sheng HeJie Wu
Sep 13, 2014·Journal of the American Chemical Society·Ayumi HaradaMasaya Sawamura

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