Efficient Access to Multifunctional Trifluoromethyl Alcohols through Base-Free Catalytic Asymmetric C-C Bond Formation with Terminal Ynamides

Angewandte Chemie
Andrea M Cook, Christian Wolf

Abstract

The asymmetric addition of terminal ynamides to trifluoromethyl ketones with a readily available chiral zinc catalyst gives CF3 -substituted tertiary propargylic alcohols in up to 99 % yield and 96 % ee. The exclusion of organozinc additives and base as well as the general synthetic utility of the products are key features of this reaction. The value of the β-hydroxy-β-trifluoromethyl ynamides is exemplified by selective transformations to chiral Z- and E-enamides, an amide, and N,O-ketene acetals. The highly regioselective hydration, stereoselective reduction, and hydroacyloxylation reactions proceed with high yields and without erosion of the ee value of the parent β-hydroxy ynamides.

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Citations

Mar 16, 2017·Journal of the American Chemical Society·Yu ZhengEric Meggers
Aug 15, 2017·Organic & Biomolecular Chemistry·Shanshan LiuMin-Can Wang
Jan 30, 2019·Angewandte Chemie·Max Moskowitz, Christian Wolf
May 28, 2019·Organic & Biomolecular Chemistry·Lucile Andna, Laurence Miesch
Aug 28, 2019·Angewandte Chemie·Barry M TrostGuillaume Mata
Jul 11, 2019·Advanced Synthesis & Catalysis·Kaluvu BalaramanChristian Wolf
Sep 9, 2016·Chemistry : a European Journal·Jun-Ichi ItoHisao Nishiyama
Aug 8, 2020·Chemistry : a European Journal·Dan JiangMin Zhang
Oct 20, 2020·Chemical Society Reviews·Ciarán C LynchChristian Wolf
Feb 19, 2021·Organic & Biomolecular Chemistry·Erhui GaoJunbiao Chang
Apr 4, 2019·Organic Letters·Steven J MansfieldEdward A Anderson
Oct 2, 2021·Chirality·Sarah E SteberChristian Wolf
Nov 2, 2021·Organic Letters·Kaluvu Balaraman, Christian Wolf

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