An Ugi Reaction Incorporating a Redox-Neutral Amine C-H Functionalization Step

Organic Letters
Zhengbo Zhu, Daniel Seidel

Abstract

Pyrrolidine and 1,2,3,4-tetrahydroisoquinoline (THIQ) undergo redox-neutral α-amidation with concurrent N-alkylation upon reaction with aromatic aldehydes and isocyanides. Reactions are promoted by acetic acid and represent a new variant of the Ugi reaction.

References

Oct 12, 2000·Angewandte Chemie·A Dömling, I Ugi
Jun 20, 2007·Chemical Society Reviews·Kevin R Campos
Dec 18, 2007·Journal of the American Chemical Society·Chen ZhangDaniel Seidel
Mar 4, 2008·Current Opinion in Chemical Biology·Irini Akritopoulou-Zanze
Jul 24, 2008·Chemical Society Reviews·Shun-Ichi Murahashi, Dazhi Zhang
Mar 19, 2009·Angewandte Chemie·Noah Z BurnsReinhard W Hoffmann
Jan 29, 2010·Journal of the American Chemical Society·Chen Zhang, Daniel Seidel
Feb 10, 2010·Chemistry : a European Journal·Rodolphe JazzarOlivier Baudoin
Nov 18, 2011·Organic Letters·Deepankar DasDaniel Seidel
Mar 23, 2012·Chemical Reviews·Alexander DömlingKan Wang
Jul 26, 2012·Chemistry : a European Journal·Emily A MitchellBert U W Maes
Sep 12, 2012·Journal of the American Chemical Society·Longle MaDaniel Seidel
Sep 29, 2012·Beilstein Journal of Organic Chemistry·Subhas Chandra Pan
Feb 27, 2013·Angewandte Chemie·Deepankar DasDaniel Seidel
Mar 21, 2013·Chemical Reviews·Christopher K PrierDavid W C MacMillan
Apr 17, 2013·Organic Letters·Magnus Rueping, Carlos Vila
Sep 13, 2013·Chemistry : a European Journal·Bo Peng, Nuno Maulide
Jan 15, 2014·Accounts of Chemical Research·Jessada Mahatthananchai, Jeffrey W Bode
Mar 13, 2014·The Journal of Organic Chemistry·Cam-Van T Vo, Jeffrey W Bode
Apr 3, 2014·Journal of the American Chemical Society·Matthew T RichersDaniel Seidel
Apr 8, 2014·Angewandte Chemie·Michael C Haibach, Daniel Seidel
May 27, 2014·Organic Letters·Weijie Chen, Daniel Seidel
Jun 24, 2014·Organic Chemistry Frontiers : an International Journal of Organic Chemistry·Daniel Seidel
Jul 18, 2014·Chemical Reviews·Benjamin H RotsteinAndrei K Yudin
Nov 25, 2014·Chemical Society Reviews·Huawen HuangHuanfeng Jiang

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Citations

Aug 12, 2016·Organic Letters·YoungKu Kang, Daniel Seidel

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