Copper(I)-Catalyzed Stereoselective Synthesis of (1E,3E)-2-Sulfonyl-1,3-dienes from N-Propargylic Sulfonohydrazones

作者: Yu Zhu , Hai-Tao Tang , Zhuang-Ping Zhan

DOI: 10.1002/ADSC.201300126

关键词:

摘要: A new method for the stereoselective synthesis of highly substituted (1E,3E)-2-sulfonyl-1,3-dienes from N-propargylic sulfonohydrazone derivatives has been developed via copper(I)-catalyzed [3,3] rearrangement and regioselective migration sulfonyl group.

参考文章(48)
Jan-E. Bäckvall, Carmen Nájera, Miguel Yus, Selenosulfonation of 1,3-dienes: One-pot synthesis of 2-(phenylsulfonyl)-1,3-dienes Tetrahedron Letters. ,vol. 29, pp. 1445- 1448 ,(1988) , 10.1016/S0040-4039(00)80320-2
David Tejedor, Gabriela Méndez-Abt, Leandro Cotos, Fernando García-Tellado, Propargyl Claisen rearrangement: allene synthesis and beyond Chemical Society Reviews. ,vol. 42, pp. 458- 471 ,(2013) , 10.1039/C2CS35311C
Thomas G. Back, Enoch K.Y. Lai, K.Raman Muralidharan, A new preparation of 3-substituted 2-(p-toluenesulfonyl)-1,3-dienes Tetrahedron Letters. ,vol. 30, pp. 6481- 6482 ,(1989) , 10.1016/S0040-4039(01)88999-1
Amy M. Danowitz, Christopher E. Taylor, Tamar M. Shrikian, Anna K. Mapp, Palladium-catalyzed [3,3]-rearrangement for the facile synthesis of allenamides. Organic Letters. ,vol. 12, pp. 2574- 2577 ,(2010) , 10.1021/OL1007845
Ana M. Martín Castro, Claisen rearrangement over the past nine decades. Chemical Reviews. ,vol. 104, pp. 2939- 3002 ,(2004) , 10.1021/CR020703U
Ming-Zhong Cai, Gui-Qin Chen, Wen-Yan Hao, Dong Wang, A facile stereoselective synthesis of 1,3-dienyl sulfones via Stille coupling reactions of (E)-α-stannylvinyl sulfones with alkenyl iodides Journal of Organometallic Chemistry. ,vol. 692, pp. 1125- 1130 ,(2007) , 10.1016/J.JORGANCHEM.2006.11.014
Petr Novák, Radek Pohl, Martin Kotora, Michal Hocek, Synthesis of C-Aryldeoxyribosides by [2 + 2 + 2]-Cyclotrimerization Catalyzed by Rh, Ni, Co, and Ru Complexes Organic Letters. ,vol. 8, pp. 2051- 2054 ,(2006) , 10.1021/OL060454M
Larry E. Overman, Lane A. Clizbe, Robert L. Freerks, Charles K. Marlowe, Thermal rearrangements of propargylic trichloroacetimidates. Synthesis of (trichloroacetamido)-1,3-dienes and -1,2-dienes Journal of the American Chemical Society. ,vol. 103, pp. 2807- 2815 ,(1981) , 10.1021/JA00400A053