Double nitro-Mannich reaction utilizing in situ generated N-trimethylsilylaldimines: novel four-component one-pot synthesis of nitroimines
作者： Seiji Tanaka , Yukinari Oguma , Yusuke Tanaka , Hidenori Echizen , Hyuma Masu
DOI: 10.1016/J.TET.2007.11.042
关键词:
摘要: Abstract Four-component synthesis of nitroimine derivatives (3) via double nitro-Mannich reaction was carried out in which nitroalkane, two moles aldehyde, and lithium hexamethyldisilazide (LHMDS) were coupled one-pot. In situ generated N-trimethylsilylaldimine reacted with nitroalkane dianion followed by the second addition resulting nitrogen anion to aldimine subsequent elimination bistrimethylsilylamine furnished nitoroimine. The proceeded erythro selectivity.
elsevier.com
sci-hub.se 参考文章(43)
Pierre Deslongchamps, Stereoelectronic effects in organic chemistry ,(1983)
Saul Patai, The chemistry of the carbon-nitrogen double bond Interscience Publishers. ,(1970)
Derek Barton, W.David Ollis, Comprehensive organic chemistry : the synthesis and reactions of organic compounds Tetrahedron Letters. ,vol. 19, ,(1978) , 10.1016/S0040-4039(01)85753-1
Henry Feuer, The chemistry of the nitro and nitroso groups Interscience Publishers. ,(1969)
Zhiping Li, Chao-Jun Li, Highly Efficient Copper-Catalyzed Nitro-Mannich Type Reaction: Cross-Dehydrogenative-Coupling between sp3 C−H Bond and sp3 C−H Bond Journal of the American Chemical Society. ,vol. 127, pp. 3672- 3673 ,(2005) , 10.1021/JA050058J
Pierre Janvier, Xiaowen Sun, Hugues Bienaymé, Jieping Zhu, Ammonium Chloride-Promoted Four-Component Synthesis of Pyrrolo[3,4-b]pyridin-5-one Journal of the American Chemical Society. ,vol. 124, pp. 2560- 2567 ,(2002) , 10.1021/JA017563A
Michael N. Paddon-Row, Nelson G. Rondan, K. N. Houk, Staggered models for asymmetric induction: attack trajectories and conformations of allylic bonds from ab initio transition structures of addition reactions Journal of the American Chemical Society. ,vol. 104, pp. 7162- 7166 ,(1982) , 10.1021/JA00389A045
Pierre Vogel, Xiaogen Huang, One-pot, four-component synthesis of polyfunctional sulfones Synthesis. ,vol. 2002, pp. 232- 236 ,(2004) , 10.1055/S-2002-19798
Kazutoshi Yamada, Seiji Tanaka, Shigeo Kohmoto, Makoto Yamamoto, Novel regioselective generation of nitroalkane dianions Journal of The Chemical Society, Chemical Communications. pp. 110- 111 ,(1989) , 10.1039/C39890000110
Alexei S. Karpov, Frank Rominger, Thomas J. J. Müller, A diversity oriented four-component approach to tetrahydro-beta-carbolines initiated by Sonogashira coupling. Organic and Biomolecular Chemistry. ,vol. 3, pp. 4382- 4391 ,(2005) , 10.1039/B511861A