Enantioselective, facially selective carbomagnesation of cyclopropenes

Journal of the American Chemical Society
Xiaozhong Liu, Joseph M Fox

Abstract

Described is the facially selective and enantioselective addition of carbon nucleophiles to prochiral 3-hydroxymethylcyclopropenes. The process creates up to four stereocenters in a tandem addition/capture sequence that combines three simple materials to give complex and diverse products. The asymmetry is induced by the inexpensive and recoverable ligand (S)-N-methylprolinol. The enantioselectivity (90-98% ee with MeMgCl) is high for a range of cyclopropenes and electrophiles. Importantly, the diastereoselectivity is complementary to that obtained by enantioselective cyclopropanation with aryldiazoacetates. High enantioselectivities are obtained only when methoxide is included in the reaction. Evidence is provided that at least two chiral ligands are involved in the enantioselectivity-determining step.

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Citations

Nov 18, 2010·Journal of the American Chemical Society·John F BrionesHuw M L Davies
Oct 30, 2010·Journal of the American Chemical Society·Diem H T PhanVy M Dong
Mar 28, 2009·Journal of the American Chemical Society·Vinod TarwadeJoseph M Fox
Oct 15, 2009·Journal of the American Chemical Society·Sébastien R Goudreau, André B Charette
Oct 15, 2008·The Journal of Organic Chemistry·Laural A Fisher, Joseph M Fox
Sep 26, 2007·Organic Letters·Stepan Chuprakov, Vladimir Gevorgyan
Oct 24, 2014·Journal of the American Chemical Society·Alejandro ParraMariola Tortosa
May 16, 2017·Angewandte Chemie·Longyang DianIlan Marek
Mar 19, 2016·Chemistry : a European Journal·Alexis ArchambeauJanine Cossy
Jun 22, 2007·Organic & Biomolecular Chemistry·Tsunehisa HirashitaShuki Araki
Nov 24, 2007·Chemistry : a European Journal·Shinji NakamuraMasanobu Uchiyama
Jan 25, 2019·Angewandte Chemie·Marc Montesinos-MagranerAbraham Mendoza
Oct 7, 2009·Chemistry : a European Journal·Louis-Philippe B BeaulieuAndré B Charette
Sep 19, 2019·Chemistry : a European Journal·Liangliang Zhang, Martin Oestreich
Apr 18, 2019·Beilstein Journal of Organic Chemistry·Marwan Simaan, Ilan Marek
Mar 19, 2013·Beilstein Journal of Organic Chemistry·Kei Murakami, Hideki Yorimitsu
Jul 12, 2007·Chemical Reviews·Michael RubinVladimir Gevorgyan
Jan 22, 2011·Organic Letters·Katja KrämerMark Lautens
Nov 23, 2018·Journal of the American Chemical Society·Yu TanHailong Yan
Sep 22, 2020·ACS Catalysis·Longyang Dian, Ilan Marek
Nov 10, 2017·Journal of the American Chemical Society·Huai-Long TengZhaomin Hou
Jun 1, 2007·Organic Letters·Samah Simaan, Ilan Marek

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