Enantioselective Synthesis of Axially Chiral Biaryls by Diels-Alder/Retro-Diels-Alder Reaction of 2-Pyrones with Alkynes.

Journal of the American Chemical Society
Meng-Meng XuQuan Cai

Abstract

The enantioselective synthesis of axially chiral biaryls by a copper-catalyzed Diels-Alder/retro-Diels-Alder reaction of 2-pyrones with alkynes is reported herein. Using electron-deficient 2-pyrones and electron-rich 1-naphthyl acetylenes as the reaction partners, a broad range of axially chiral biaryl esters are obtained in excellent yields (up to 97% yield) and enantioselectivities (up to >99% ee). DFT calculations reveal the reaction mechanism and provide insights into the origins of the stereoselectivities. The practicality and robustness of this reaction are showcased by gram-scale synthesis. The synthetic utilizations are demonstrated by the amenable transformations of the products.

References

Sep 29, 2000·Organic Letters·I E MarkoB Augustyns
Aug 14, 2003·Chemical Reviews·Yu ChenAndrei K Yudin
Aug 24, 2005·Angewandte Chemie·Gerhard BringmannMatthias Breuning
May 2, 2007·Journal of the American Chemical Society·Yi WangLi Deng
Apr 4, 2008·Organic & Biomolecular Chemistry·Takanori Shibata, Kyoji Tsuchikama
May 6, 2009·Journal of the American Chemical Society·Julian Ying-Teck Soh, Choon-Hong Tan
Jul 29, 2009·Angewandte Chemie·Jonathan ClaydenSteven R LaPlante
Oct 23, 2009·Chemical Society Reviews·Marisa C KozlowskiElizabeth C Linton
Oct 14, 2010·Chemical Reviews·Gerhard BringmannMatthias Breuning
Dec 15, 2010·Journal of the American Chemical Society·Fenghai GuoRegan J Thomson
Mar 2, 2011·ChemMedChem·Steven R LaPlanteOliver Hucke
Mar 25, 2011·Chemical Society Reviews·Gema Domínguez, Javier Pérez-Castells
Aug 19, 2011·Journal of Medicinal Chemistry·Steven R LaplantePaul J Edwards
Dec 17, 2011·Chemical Science·Keith J BartelsonLi Deng
Jan 12, 2013·Chemistry : a European Journal·Patrick BurchKarl Gademann
Mar 2, 2013·Angewandte Chemie·Seiji Shirakawa, Keiji Maruoka
Apr 27, 2013·Chirality·Arie ZaskGeorge A Ellestad
May 11, 2013·Journal of the American Chemical Society·Gong-Qiang LiLászló Kürti
Apr 24, 2015·Chemical Society Reviews·J Wencel-DelordF Colobert
Aug 19, 2015·Natural Product Reports·Jamie E SmythPaul A Keller
Nov 13, 2015·Journal of the American Chemical Society·Ye-Hui ChenBin Tan
May 12, 2016·Angewandte Chemie·Vincent C Fäseke, Christof Sparr
Sep 7, 2016·Journal of the American Chemical Society·Pedro Ramírez-LópezJosé M Lassaletta
Jan 21, 2017·Journal of the American Chemical Society·Lei ZhangBin Tan
Jan 21, 2017·Journal of the American Chemical Society·Vivek S RautJean Rodriguez
Jan 27, 2017·Angewandte Chemie·Zhi-Jun JiaHerbert Waldmann
Sep 6, 2017·Chemistry : a European Journal·Reto M WitzigChristof Sparr

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