Rhodium-catalyzed dynamic kinetic asymmetric transformations of racemic tertiary allylic trichloroacetimidates with anilines

Journal of the American Chemical Society
Jeffrey S Arnold, Hien M Nguyen

Abstract

The rhodium-catalyzed regio- and enantioselective amination of racemic tertiary allylic trichloroacetimidates with a variety of aniline nucleophiles is a direct and efficient route to chiral α,α-disubstituted allylic N-arylamines. We describe the first dynamic kinetic asymmetric transformations of racemic tertiary allylic electrophiles with anilines utilizing a chiral diene-ligated rhodium catalyst. The method allows for the formation of α,α-disubstituted allylic N-arylamines in moderate to good yields with good to excellent levels of regio- and enantioselectivity.

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Citations

Nov 7, 2015·Organic Letters·Jongrock KongRyan Mondschein
Sep 9, 2015·Journal of the American Chemical Society·Qi ZhangHien M Nguyen
Apr 22, 2017·Chemical Communications : Chem Comm·Zheng LingWanbin Zhang
Jun 9, 2015·Chemical Communications : Chem Comm·Kun XuBernhard Breit
Apr 19, 2019·Angewandte Chemie·Koji TakizawaShigeki Matsunaga
Nov 14, 2019·Organic & Biomolecular Chemistry·Rima ThakurAmit Kumar
Sep 14, 2016·Chemistry : a European Journal·Changkun Li, Bernhard Breit
Jun 12, 2013·Angewandte Chemie·Guoqiang Yang, Wanbin Zhang
May 15, 2021·Journal of the American Chemical Society·Wusheng GuoShaofei Ni
Apr 3, 2020·Organic Letters·Kodai SaitoTakahiko Akiyama
Jul 6, 2019·Journal of the American Chemical Society·Samir GhoraiChangkun Li
May 11, 2013·Journal of the American Chemical Society·Genping HuangFahmi Himo
Jan 9, 2015·The Journal of Organic Chemistry·Daniel R WallachJohn D Chisholm
Jun 25, 2015·Journal of the American Chemical Society·Qing-An ChenVy M Dong
Nov 18, 2017·The Journal of Organic Chemistry·Elisabet SelvaDavid Guijarro
Jan 6, 2018·Journal of the American Chemical Society·Matthew R PorterJoseph J Topczewski
May 26, 2018·Journal of the American Chemical Society·Sheng-Biao TangShu-Li You
Apr 18, 2020·Organic Letters·Samir GhoraiChangkun Li

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