One-pot organocatalytic domino Michael-aldol and intramolecular SN2 reactions. Asymmetric synthesis of highly functionalized epoxycyclohexanone derivatives

Journal of the American Chemical Society
Mauro MarigoKarl Anker Jørgensen

Abstract

The development of the organocatalytic asymmetric one-pot Michael-Darzens condensation giving highly functionalized complex epoxycyclohexanone derivatives with up to four chiral centers is presented. Depending on the reaction conditions, either the polysubstituted 7-oxa-bicyclo[4.1.0]heptan-2-one ring system or 2-chloro-cyclohex-2-enone derivatives can be formed. For the former class of compounds a high diversity in substitution pattern is demonstrated, and the optically active products are obtained in excellent diastereo- and enantioselectivities. The potential synthetic applications of the products have been demonstrated by performing a series of highly diastereoselective transformations leading to optically active products useful for the life-science industry. Furthermore, mechanistic investigations on the formation of the chiral centers in the optically active epoxycyclohexanone are presented.

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Citations

May 28, 2011·Chemical Reviews·Albert Moyano, Ramon Rios
Dec 1, 2006·Chemical Communications : Chem Comm·Armando CarloneKarl Anker Jørgensen
Aug 12, 2009·Chemical Communications : Chem Comm·Srivari ChandrasekharBharatam Jagadeesh
Jul 20, 2010·Proceedings of the National Academy of Sciences of the United States of America·Claire M FillouxTomislav Rovis
Apr 23, 2013·Chemistry & Biology·Andrey P AntonchickHerbert Waldmann
Apr 20, 2017·Chembiochem : a European Journal of Chemical Biology·Tim FörsterHerbert Waldmann
May 15, 2015·Chemical Communications : Chem Comm·A Quintard, J Rodriguez
Jun 6, 2008·Chemistry : a European Journal·Patrick T FrankeKarl Anker Jørgensen
Dec 15, 2012·Chemistry, an Asian Journal·Hailong ZhangRui Wang
Nov 14, 2017·Angewandte Chemie·Jeremy D Mason, Steven M Weinreb
Nov 30, 2006·Angewandte Chemie·Claudio Palomo, Antonia Mielgo
Dec 30, 2006·Angewandte Chemie·Armando CarloneKarl Anker Jørgensen
Jan 17, 2007·Angewandte Chemie·Dieter EndersMatthias R M Hüttl
Nov 21, 2007·Organic & Biomolecular Chemistry·Sirirat KumarnSteven V Ley
Feb 1, 2008·Angewandte Chemie·Scott E Denmark, Gregory L Beutner
Jan 30, 2008·Chemistry : a European Journal·Jan VeselyArmando Córdova
Jun 6, 2008·Organic & Biomolecular Chemistry·Xinhong Yu, Wei Wang
May 28, 2008·Chemistry, an Asian Journal·Antonia Mielgo, Claudio Palomo
Jun 26, 2008·Angewandte Chemie·Magnus Rueping, Andrey P Antonchick
Oct 22, 2008·Organic & Biomolecular Chemistry·C B Shinisha, Raghavan B Sunoj
Dec 19, 2008·Angewandte Chemie·Johan Franzén, Andreas Fisher
Apr 9, 2009·Chemistry, an Asian Journal·Mahendra P Patil, Raghavan B Sunoj
Sep 18, 2009·Chemistry : a European Journal·Chun-Li CaoJie Sun

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