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 |
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| Authors: | Amparo Sanz‐Marco Andrea García‐Ortiz Prof. Dr. Gonzalo Blay Isabel Fernández Prof. Dr. José R. Pedro |
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| Affiliation: | Department de Química Orgànica‐Facultat de Química, Universitat de València, C/Dr. Moliner 50, 46100 Burjassot (València) (Spain), Fax: (+34)?963544328 |
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| 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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| Keywords: | alkynes asymmetric catalysis conjugate addition enones fluorine compounds |
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