Asymmetric construction of quaternary stereocenters by direct organocatalytic amination of alpha-substituted alpha-cyanoacetates and beta-dicarbonyl compounds

Journal of the American Chemical Society
Steen SaabyKarl Anker Jørgensen

Abstract

The first organocatalytic highly enantioselective reactions of substituted alpha-cyanoacetates and beta-dicarbonyl compounds with azodicarboxylates are reported. In the presence of 0.1-5 mol % of a quinidine-derived alkaloid beta-ICD, optically active quaternary hydrazine adducts are obtained in very high yields and with enantioselectivities up to >98% ee. A two-step procedure for the cleavage of the hydrazine N-N bond using SmI2 is also demonstrated.

References

May 16, 2002·Journal of the American Chemical Society·Benjamin List
May 30, 2002·Journal of the American Chemical Society·Nagaswamy KumaragurubaranKarl Anker Jørgensen
Oct 31, 2002·Angewandte Chemie·Jens Christoffers, Alexander Mann
Apr 3, 2003·Angewandte Chemie·Mauro MarigoKarl Anker Jørgensen
Jun 6, 2003·Journal of the American Chemical Society·Norie Momiyama, Hisashi Yamamoto
Feb 10, 2004·Chemistry : a European Journal·Rosario FernándezJosé M Lassaletta
Oct 14, 2005·Journal of the American Chemical Society·Mark S Taylor, Eric N Jacobsen

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Citations

Jun 23, 2010·Proceedings of the National Academy of Sciences of the United States of America·Giorgio BencivenniPaolo Melchiorre
Dec 18, 2012·Beilstein Journal of Organic Chemistry·Pankaj Chauhan, Swapandeep Singh Chimni
Jan 3, 2007·Drug Discovery Today·Matthew J GauntNgoc T Vo
Jul 28, 2016·Chemical Reviews·Thavendran GovenderTricia Naicker
Oct 9, 2007·Chemistry : a European Journal·Peter DinérKarl Anker Jørgensen
Aug 12, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Llorenç BenaventMelania Gómez-Martínez
Feb 20, 2018·Chemistry : a European Journal·Jingchuan ZhangXiaoming Feng
Jan 27, 2016·Chemical Communications : Chem Comm·Isai RamakrishnaMahiuddin Baidya
Nov 1, 2013·Chemistry : a European Journal·Yoshito NakamotoSusumi Hatakeyama
Aug 8, 2017·Angewandte Chemie·Dhevalapally B RamacharyGuguloth Thirupathi
Mar 26, 2010·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Tirayut Vilaivan, Worawan Bhanthumnavin
May 27, 2006·Organic & Biomolecular Chemistry·Tian-Yu LiuYing-Chun Chen
Oct 20, 2006·Angewandte Chemie·Tommaso MarcelliHenk Hiemstra
Nov 11, 2006·Angewandte Chemie·Ryosuke Matsubara, Shū Kobayashi
Feb 25, 2005·Chemistry : a European Journal·Burkard KreidlerJens Christoffers
Nov 21, 2007·Organic & Biomolecular Chemistry·Sirirat KumarnSteven V Ley
Sep 25, 2007·Chemistry : a European Journal·Marjan Jereb, Antonio Togni
Jan 1, 2008·Chemistry, an Asian Journal·Yujiro HayashiTadafumi Uchimaru
Apr 17, 2008·Chemistry, an Asian Journal·Vijay NairBeneesh Pattoorpadi Babu
Sep 2, 2005·Angewandte Chemie·Giuseppe BartoliLetizia Sambri
Jan 24, 2006·Angewandte Chemie·Tommaso MarcelliHenk Hiemstra
Feb 24, 2006·Angewandte Chemie·Mark S Taylor, Eric N Jacobsen

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