Synergistic gold and enamine catalysis: intermolecular α-alkylation of aldehydes with allenamides

Chemical Communications : Chem Comm
Jaime Fernández-CasadoFernando López

Abstract

Aldehydes can be α-alkylated with allenamides by the combined action of an organocatalyst and a gold complex. The reaction requires the simultaneous generation of an enamine and a gold-activated allenamide. Importantly, by using a chiral amine as organocatalyst it is possible to obtain aldehyde products featuring all-carbon quaternary stereocenter at their α-position, with moderate to good levels of enantioselectivity.

References

Oct 22, 2003·Accounts of Chemical Research·Lin-Li WeiRichard P Hsung
Jan 15, 2004·Journal of the American Chemical Society·Nicola Vignola, Benjamin List
Mar 31, 2007·Science·Teresa D BeesonDavid W C Macmillan
Jan 22, 2009·Angewandte Chemie·Pier Giorgio CozziLuca Zoli
Oct 23, 2009·Chemical Society Reviews·Alois Fürstner
Dec 31, 2009·Angewandte Chemie·A Stephen K Hashmi, Christoph Hubbert
Jun 24, 2010·Journal of the American Chemical Society·Adam R BrownEric N Jacobsen
Sep 14, 2010·Journal of the American Chemical Society·Hui-Wen ShihDavid W C MacMillan
Aug 19, 2011·Accounts of Chemical Research·Kim L JensenKarl Anker Jørgensen
Sep 15, 2011·Beilstein Journal of Organic Chemistry·Dawei WangXiaodong Shi
Apr 21, 2012·Chemical Science·Anna E Allen, David W C Macmillan
Jun 15, 2012·Chemistry : a European Journal·Charles C J Loh, Dieter Enders
Nov 17, 2012·Chemical Society Reviews·Zhenting Du, Zhihui Shao
Apr 5, 2013·Chemical Reviews·Ting LuRichard P Hsung
May 17, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Paul C YoungAi-Lan Lee
Jul 31, 2013·Journal of the American Chemical Society·Jason M Stevens, David W C MacMillan
Oct 12, 2013·Chemistry : a European Journal·Sergi MontserratGregori Ujaque
Nov 26, 2013·Angewandte Chemie·Benjamin ListManuel van Gemmeren
Feb 11, 2014·Journal of the American Chemical Society·Simon KrautwaldErick M Carreira
Mar 19, 2014·Chemical Communications : Chem Comm·Yongming DengHong Wang
Mar 29, 2014·Chemical Society Reviews·Weibo Yang, A Stephen K Hashmi
Mar 29, 2014·Chemistry, an Asian Journal·Andrea GualandiPier Giorgio Cozzi
Jun 14, 2014·Angewandte Chemie·Alexander Zhdanko, Martin E Maier
Aug 19, 2014·Journal of the American Chemical Society·Zhaofeng WangYong Huang
Apr 7, 2015·Chemical Reviews·Ruth Dorel, Antonio M Echavarren
Jul 3, 2015·Journal of the American Chemical Society·Haihui PengXiaodong Shi

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Citations

Feb 28, 2017·Journal of the American Chemical Society·Han ZhouSanzhong Luo
Oct 26, 2018·Chemistry : a European Journal·Danila GasperiniAndrew D Smith
Oct 8, 2019·Chemistry, an Asian Journal·Shashank P SanchetiNitin T Patil
Nov 26, 2019·Topics in Current Chemistry·Pier Giorgio CozziGiacomo Rodeghiero
Mar 3, 2018·Organic Letters·Ryosuke HaraguchiShin-Ichi Fukuzawa
Sep 9, 2021·Chemistry : a European Journal·Leo D M Nicholls, Helma Wennemers

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