Indium-Catalyzed Amide Allylation of N-Carbonyl Imides: Formation of Azaspiro-γ-lactones via Ring Opening-Reclosure.
作者： Tetsuya Sengoku , Yusuke Murata , Yuwa Aso , Ai Kawakami , Toshiyasu Inuzuka
DOI: 10.1021/ACS.ORGLETT.5B03021
关键词: Aza Compounds 、 Medicinal chemistry 、 Ring (chemistry) 、 Stereochemistry 、 Amide 、 Molecule 、 Chemistry 、 Zinc compounds 、 Catalysis 、 Indium
摘要: A novel and facile synthesis of azaspiro-γ-lactones with a methylene-lactam framework from N-carbonyl imides is described. Mechanistic investigations provide evidence for two-step reaction process involving ZnCl(2)-promoted addition β-amido allylindium species followed by an unexpectedly molecular-sieves-mediated ring opening-reclosure concomitantly the loss unit.
acs.org
sci-hub.se 参考文章(29)
Masaki Takahashi, Yusuke Murata, Masahiro Ishida, Fumitoshi Yagishita, Masami Sakamoto, Tetsuya Sengoku, Hidemi Yoda, Catalytic amide allylation of α-ketoesters: extremely high enantioselective synthesis of ester functionalised α-methylene-γ-butyrolactones. Organic and Biomolecular Chemistry. ,vol. 12, pp. 7686- 7689 ,(2014) , 10.1039/C4OB01508H
Noriaki Asakura, Tsukasa Hirokane, Hayato Hoshida, Hidetoshi Yamada, Molecular sieves 5A as an acidic reagent: the discovery and applications Tetrahedron Letters. ,vol. 52, pp. 534- 537 ,(2011) , 10.1016/J.TETLET.2010.11.113
Laurent Chabaud, Philippe James, Yannick Landais, Allylsilanes in Organic Synthesis − Recent Developments European Journal of Organic Chemistry. ,vol. 2004, pp. 3173- 3199 ,(2004) , 10.1002/EJOC.200300789
Hua-Xing Huo, Jeremy R. Duvall, Meng-Yuan Huang, Ran Hong, Catalytic asymmetric allylation of carbonyl compounds and imines with allylic boronates Organic chemistry frontiers. ,vol. 1, pp. 303- 320 ,(2014) , 10.1039/C3QO00081H
Makoto Yasuda, Masahiko Haga, Akio Baba, Isolation and Characterization of a Nucleophilic Allylic Indium Reagent Organometallics. ,vol. 28, pp. 1998- 2000 ,(2009) , 10.1021/OM900096R
Itaru Suzuki, Kensuke Kiyokawa, Makoto Yasuda, Akio Baba, Indium(III) Halide-Catalyzed UV-Irradiated Radical Coupling of Iodomethylphosphorus Compounds with Various Organostannanes Organic Letters. ,vol. 15, pp. 1728- 1731 ,(2013) , 10.1021/OL4005257
R. W. Hoffmann, α-Chiral allylboronates: reagents for asymmetric synthesis Pure and Applied Chemistry. ,vol. 60, pp. 123- 130 ,(1988) , 10.1351/PAC198860010123
Takashi Tsuji, Shin-ichi Usugi, Hideki Yorimitsu, Hiroshi Shinokubo, Seijiro Matsubara, Koichiro Oshima, Allylation of Carbonyl Compounds with Allylic Gallium Reagents Chemistry Letters. ,vol. 2002, pp. 2- 3 ,(2002) , 10.1246/CL.2002.2
Yoshinori. Yamamoto, Naoki. Asao, SELECTIVE REACTIONS USING ALLYLIC METALS Chemical Reviews. ,vol. 93, pp. 2207- 2293 ,(1993) , 10.1021/CR00022A010
Shuki Araki, Tomoaki Horie, Motoshi Kato, Tsunehisa Hirashita, Hatsuo Yamamura, Masao Kawai, Regioselective allylation and alkylation of electron-deficient alkenes with organogallium and organoindium reagents Tetrahedron Letters. ,vol. 40, pp. 2331- 2334 ,(1999) , 10.1016/S0040-4039(99)00179-3