Rhodium-catalyzed asymmetric construction of quaternary carbon stereocenters: ligand-dependent regiocontrol in the 1,4-addition to substituted maleimides

Journal of the American Chemical Society
Ryo ShintaniTamio Hayashi

Abstract

A rhodium-catalyzed asymmetric 1,4-addition of arylboronic acids to substituted maleimides has been described. The regioselectivity in this reaction is controlled by the choice of ligand (dienes or bisphosphines), and 1,4-adducts with a quaternary stereocenter can be obtained with high regio- and enantioselectivity by the use of (R)-H8-binap.

References

Oct 31, 2002·Angewandte Chemie·Jens Christoffers, Alexander Mann
Aug 14, 2003·Chemical Reviews·Tamio Hayashi, Kaori Yamasaki
Jan 16, 2004·Proceedings of the National Academy of Sciences of the United States of America·Christopher J Douglas, Larry E Overman
Feb 12, 2004·Journal of the American Chemical Society·Christian FischerErick M Carreira
Jan 6, 2005·Journal of the American Chemical Society·Ryo ShintaniTamio Hayashi
Jun 22, 2005·Chemical Communications : Chem Comm·Ryo ShintaniTamio Hayashi
Aug 4, 2005·Journal of the American Chemical Society·Jean-François PaquinErick M Carreira
Feb 2, 2006·Journal of the American Chemical Society·Hirokazu TsukamotoYoshinori Kondo
Mar 2, 1998·Angewandte Chemie·Elias J Corey, Angel Guzman-Perez

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Citations

Mar 30, 2007·Chemical Communications : Chem Comm·Gui-Ling ZhaoArmando Córdova
Aug 25, 2010·Chemical Communications : Chem Comm·Christine Hawner, Alexandre Alexakis
Jun 14, 2016·Organic Process Research & Development·Samantha E ShockleyBrian M Stoltz
Sep 14, 2016·Organic Letters·Yang Xiong, Guozhu Zhang
Feb 15, 2007·Chemical Communications : Chem Comm·Tomoya Miura, Masahiro Murakami
Jun 18, 2017·Organic & Biomolecular Chemistry·Marcos VeguillasM Carmen Carreño
Aug 23, 2016·Chemical Communications : Chem Comm·Luca S Dobson, Graham Pattison
Apr 26, 2012·Chemistry : a European Journal·Aditya L GottumukkalaAdriaan J Minnaard
Jul 5, 2006·Angewandte Chemie·Giuseppe BartoliPaolo Melchiorre
Dec 18, 2007·Angewandte Chemie·Jeffrey B Johnson, Tomislav Rovis
May 7, 2008·Angewandte Chemie·Christian DefieberErick M Carreira
Apr 22, 2010·Chemical Society Reviews·Hannah J EdwardsChristopher G Frost
Jul 28, 2010·Angewandte Chemie·Jian ZhangSoon Hyeok Hong
May 30, 2019·Organic & Biomolecular Chemistry·Graham Pattison
Dec 17, 2014·Nature·Kyle W Quasdorf, Larry E Overman

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