Asymmetric fluorination of enamides: access to α-fluoroimines using an anionic chiral phase-transfer catalyst

Journal of the American Chemical Society
Robert J PhippsF Dean Toste

Abstract

The use of a BINOL-derived phosphate as a chiral anionic phase-transfer catalyst in a nonpolar solvent allows the enantioselective fluorination of enamides using Selectfluor as the fluorinating reagent. We demonstrate that a wide range of stable and synthetically versatile α-(fluoro)benzoylimines can be readily accessed with high enantioselectivity. These compounds have the potential to be readily elaborated into a range of highly stereodefined β-fluoroamines, compounds that constitute highly valuable building blocks of particular importance in the synthesis of pharmaceuticals.

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Citations

Sep 18, 2015·Journal of the American Chemical Society·Ying HeF Dean Toste
Aug 8, 2015·Journal of the American Chemical Society·Hiromichi EgamiYoshitaka Hamashima
Aug 8, 2013·Proceedings of the National Academy of Sciences of the United States of America·Jeffrey WuF Dean Toste
Jul 5, 2016·Chemical & Pharmaceutical Bulletin·Takeo SakaiYuji Mori
Jul 30, 2016·Journal of the American Chemical Society·Zhenyu YangF Dean Toste
Oct 18, 2016·Journal of the American Chemical Society·Brandon A Vara, Jeffrey N Johnston
Dec 14, 2016·Journal of the American Chemical Society·Sachin NaruteDoron Pappo
Jul 25, 2012·Nature Chemistry·Robert J PhippsF Dean Toste
Mar 2, 2013·Angewandte Chemie·Seiji Shirakawa, Keiji Maruoka
Oct 26, 2018·Chemistry : a European Journal·Deyun Qian, Jianwei Sun
Jan 27, 2018·Nature Communications·Siyu PengYong Huang
May 9, 2019·Chemical Communications : Chem Comm·Philip J ChevisStephen G Pyne
Jan 3, 2013·Angewandte Chemie·Manuel Mahlau, Benjamin List
Jul 23, 2013·Angewandte Chemie·Theresa LiangTobias Ritter
Sep 15, 2017·Beilstein Journal of Organic Chemistry·Johannes SchörgenhumerMario Waser
Jun 2, 2020·Chemical & Pharmaceutical Bulletin·Hiromichi Egami
Jun 24, 2020·Organic & Biomolecular Chemistry·Yi-Feng WangDan-Qian Xu
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Feb 26, 2015·Chemistry : a European Journal·Fedor Romanov-MichailidisAlexandre Alexakis

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