Expedient synthesis of highly substituted pyrroles via tandem rearrangement of α-diazo oxime ethers

作者: Yaojia Jiang , Wei Chuen Chan , Cheol-Min Park

DOI: 10.1021/JA300552C

关键词:

摘要: An efficient rhodium-catalyzed synthesis of 2H-azirines and pyrroles has been developed. Novel rearrangement α-oximino ketenes derived from α-diazo oxime ethers provides bearing quaternary centers allows for subsequent to highly substituted in excellent yields.

参考文章(50)
Patrice Fontaine, Géraldine Masson, Jieping Zhu, Synthesis of pyrroles by consecutive multicomponent reaction/[4 + 1] cycloaddition of alpha-iminonitriles with isocyanides. Organic Letters. ,vol. 11, pp. 1555- 1558 ,(2009) , 10.1021/OL9001619
Hui Fan, Jiangnan Peng, Mark T. Hamann, Jin-Feng Hu, Lamellarins and related pyrrole-derived alkaloids from marine organisms. Chemical Reviews. ,vol. 108, pp. 264- 287 ,(2008) , 10.1021/CR078199M
Hajime Seki, Gunda I. Georg, Synthesis of amino acid derived enaminones via Wolff rearrangement using vinylogous amides as carbon nucleophiles. Journal of the American Chemical Society. ,vol. 132, pp. 15512- 15513 ,(2010) , 10.1021/JA107329K
Masaki Fujita, Yoichi Nakao, Shigeki Matsunaga, Motoharu Seiki, Yoshifumi Itoh, Jun Yamashita, Rob W. M. van Soest, Nobuhiro Fusetani, Ageladine A: an antiangiogenic matrixmetalloproteinase inhibitor from the marine sponge Agelas nakamurai. Journal of the American Chemical Society. ,vol. 125, pp. 15700- 15701 ,(2003) , 10.1021/JA038025W
Brian A Johns, Kristjan S Gudmundsson, Elizabeth M Turner, Scott H Allen, David K Jung, Connie J Sexton, F.Leslie Boyd, Michael R Peel, Pyrazolo[1,5-a]pyridines: synthetic approaches to a novel class of antiherpetics Tetrahedron. ,vol. 59, pp. 9001- 9011 ,(2003) , 10.1016/J.TET.2003.02.003
Verónica Estévez, Mercedes Villacampa, J. Carlos Menéndez, Multicomponent reactions for the synthesis of pyrroles Chemical Society Reviews. ,vol. 39, pp. 4402- 4421 ,(2010) , 10.1039/B917644F
Girija S. Singh, Matthias D'hooghe, Norbert De Kimpe, Synthesis and reactivity of C-heteroatom-substituted aziridines. Chemical Reviews. ,vol. 107, pp. 2080- 2135 ,(2007) , 10.1021/CR0680033
Richmond Sarpong, Julius T. Su, Brian M. Stoltz, The Development of a Facile Tandem Wolff/Cope Rearrangement for the Synthesis of Fused Carbocyclic Skeletons Journal of the American Chemical Society. ,vol. 125, pp. 13624- 13625 ,(2003) , 10.1021/JA037587C