Iridium-Catalyzed Enantioselective Fluorination of Racemic, Secondary Allylic Trichloroacetimidates

Journal of the American Chemical Society
Qi ZhangHien M Nguyen

Abstract

The Ir-catalyzed enantioselective fluorination of racemic, branched allylic trichloroacetimidates with Et3N·3HF is a mild and efficient route for selective incorporation of fluoride ion into allylic systems. We herein describe the asymmetric fluorination of racemic, secondary allylic electrophiles with Et3N·3HF using a chiral-diene-ligated Ir complex. The methodology enables the formation of acyclic fluorine-containing compounds in good yields with excellent levels of asymmetric induction and overcomes the limitations previously associated with the enantioselective construction of secondary allylic fluorides bearing α-linear substituents.

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Citations

Jun 25, 2016·Chemical Reviews·David A PetroneMark Lautens
Aug 17, 2016·Journal of the American Chemical Society·Deng-Fu LuHao Xu
Mar 8, 2017·Journal of the American Chemical Society·Simon L RösslerErick M Carreira
Jun 3, 2017·Journal of the American Chemical Society·Amy A OttJoseph J Topczewski
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Sep 16, 2017·Angewandte Chemie·Cheng-Qiang WangChao Feng
Nov 5, 2016·Angewandte Chemie·T Andrew McTeague, Timothy F Jamison
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Sep 25, 2017·Accounts of Chemical Research·Jianping Qu, Günter Helmchen
Dec 24, 2018·Organic Letters·Jason C MixdorfHien M Nguyen
Jul 6, 2019·Journal of the American Chemical Society·Samir GhoraiChangkun Li
Jan 6, 2018·Journal of the American Chemical Society·Matthew R PorterJoseph J Topczewski
Dec 26, 2018·Chemical Reviews·Qiang ChengShu-Li You

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