Phosphahelicenes in asymmetric organocatalysis: [3+2] cyclizations of γ-substituted allenes and electron-poor olefins

Angewandte Chemie
Maxime GicquelAngela Marinetti

Abstract

The first use of phosphahelicene in enantioselective organocatalysis is reported. New chiral phosphahelicenes have been prepared and enable highly enantioselective [3+2] cyclization reactions between arylidene- or alkylidenemalononitriles and γ-substituted allenoates or cyanoallenes. These reactions afford cyclopentene derivatives in both high yields and diastereoselectivities, with enantiomeric excesses of up to 97 %.

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Citations

Apr 15, 2016·Journal of the American Chemical Society·Takazumi KatayamaTakuji Hatakeyama
Jun 11, 2016·Journal of the American Chemical Society·Zhijian HuangYonggui Robin Chi
Sep 23, 2016·Journal of the American Chemical Society·Xiao-Ye WangKlaus Müllen
Jan 24, 2017·Journal of the American Chemical Society·Elisa González-FernándezManuel Alcarazo
Apr 20, 2017·Organic & Biomolecular Chemistry·Hai-Lei CuiXiao-Jie Jiang
Aug 16, 2016·Chemistry : a European Journal·Yuichiro TokoroShin-Ichi Fukuzawa
May 8, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Ayana WakatsukiYoshihiro Matano
Jun 16, 2016·Organic & Biomolecular Chemistry·Dhevalapally B RamacharyT Prabhakar Reddy
Aug 2, 2016·Chemical Society Reviews·Mathieu DutartreSylvain Jugé
Jul 14, 2016·Organic & Biomolecular Chemistry·Jasneet KaurSwapandeep Singh Chimni
Nov 10, 2018·Organic & Biomolecular Chemistry·Qiang WangXuesen Fan
Feb 5, 2019·Chemistry : a European Journal·Keihann YavariJeanne Crassous
May 16, 2019·Organic & Biomolecular Chemistry·Jian-Qiang ZhaoWei-Cheng Yuan
Dec 19, 2019·Chemical Communications : Chem Comm·Er-Qing Li, You Huang
Oct 5, 2019·Chemistry : a European Journal·Julie FebvayAngela Marinetti
Apr 24, 2016·Chemistry : a European Journal·David SchweinfurthFrançois Diederich
Jan 6, 2021·The Journal of Organic Chemistry·Jianning LiaoHongchao Guo
Apr 17, 2019·Organic Letters·Md Shafiqur Rahman, Naohiko Yoshikai

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