Asymmetric binary-acid catalysis with chiral phosphoric acid and MgF(2): catalytic enantioselective Friedel-Crafts reactions of beta,gamma-unsaturated alpha-ketoesters

Organic Letters
Jian LvJin-Pei Cheng

Abstract

A unique binary chiral phosphoric acid 1a/MgF(2) catalyst that enables effective catalysis of asymmetric Friedel-Crafts reactions of phenols with up to 82% yield and >99% ee is presented. A dramatic synergistic effect has been observed in the combinations of two types of acids, wherein a highly active binary-acid catalyst can be generated from two individually inert acids.

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Citations

Jun 12, 2013·Chemical Reviews·Giovanni DesimoniPaolo Quadrelli
May 17, 2012·Acta Crystallographica. Section E, Structure Reports Online·Jia YeYu Cheng
Nov 26, 2015·Journal of the American Chemical Society·Jian LvSanzhong Luo
May 18, 2017·Organic & Biomolecular Chemistry·Hélène Pellissier
Jan 15, 2016·Chemistry, an Asian Journal·Linqing WangRui Wang
Aug 1, 2012·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Ryo Gotoh, Masahiro Yamanaka
Jun 18, 2016·Chemical Communications : Chem Comm·Dan LiDongxu Yang
Nov 27, 2014·Chemical Communications : Chem Comm·Audrey DumoulinGéraldine Masson
Nov 7, 2015·Chemistry : a European Journal·Masaru KatoKazuo Nagasawa
Jun 13, 2018·Organic & Biomolecular Chemistry·Abdul Rahman, Xufeng Lin
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Nov 5, 2011·Chemistry : a European Journal·Marion BarbazangesCyril Ollivier
Nov 15, 2012·Chemical Communications : Chem Comm·Jian Lv, Sanzhong Luo
Jan 3, 2013·Angewandte Chemie·Manuel Mahlau, Benjamin List
Jun 27, 2014·Chemical Communications : Chem Comm·Renta Jonathan ChewPak-Hing Leung
Oct 30, 2012·Dalton Transactions : an International Journal of Inorganic Chemistry·Shinobu TakizawaHiroaki Sasai
May 10, 2012·Organic & Biomolecular Chemistry·Alejandro ParraJosé Alemán

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