One-pot reductive coupling of N-acylcarbamates with activated alkenes: application to the asymmetric synthesis of pyrrolo[1,2-a]azepin-5-one ring system and (-)-xenovenine

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	One-pot reductive coupling of N-acylcarbamates with activated alkenes: application to the asymmetric synthesis of pyrrolo[1,2-a]azepin-5-one ring system and (-)-xenovenine
	Liu, Xue-Kui ; Zheng, Xiao ; Ruan, Yuan-Ping ; Ma, Jie ; Huang, Pei-Qiang ; Huang PQ(黄培强)
刊名	http://dx.doi.org/10.1039/c1ob06697h
	2012
关键词	INTERMOLECULAR ADDITION-REACTIONS TERT-BUTANESULFINYL IMINES MADAGASCAN FROGS MANTELLA N,O-ACETAL TMS ETHER NICOTINIC ACETYLCHOLINE-RECEPTOR TETRAMIC ACID-DERIVATIVES NATURAL-PRODUCT SYNTHESIS SILYL KETENE ACETALS BETA-AMINO ALCOHOLS SAMARIUM DII
英文摘要	National Basic Research Program (973 Program) of China [2010CB833200]; NSF of China [20402012, 20832005]; Natural Science Foundation of Fujian Province of China [2010J01050]; Fundamental Research Funds for the Central Universities of China [201112G001]; The one-pot reductive coupling of N-acylcarbamates with activated alkenes is described. The method is based on partial reduction of N-acylcarbamates with DIBAL-H, followed by N-acyliminium ion formation and SmI2-mediated radical coupling with activated alkenes. Both acyclic and cyclic N-acylcarbamates can be used as stable substrates, and a range of activated alkenes serve as effective radical receptors. The reductive coupling of L-N-acylcarbamates 12/13 gave 2,5-disubstituted pyrrolidine derivatives in high trans-diastereoselectivities. The reductive coupling with penta-2,4-dienoate proceeded exclusively in a 1,6-addition fashion, producing a single non-conjugated E-isomer. On the basis of this method, a three-step construction of pyrrolo[1,2-a]azepin-5-one 16, the skeleton of many stemona alkaloids and lehmizidine alkaloids, and a seven-step synthesis of (-)-xenovenine (pyrrolizidine cis-223H, ent-6), the unnatural enantiomer of the frog/ant venom alkaloid possessing potent inhibitory activity towards nAChR channel, were achieved starting from L-12.
语种	英语
内容类型	期刊论文
源URL	[http://dspace.xmu.edu.cn/handle/2288/64406]
专题	化学化工－已发表论文
推荐引用方式 GB/T 7714	Liu, Xue-Kui,Zheng, Xiao,Ruan, Yuan-Ping,et al. One-pot reductive coupling of N-acylcarbamates with activated alkenes: application to the asymmetric synthesis of pyrrolo[1,2-a]azepin-5-one ring system and (-)-xenovenine[J]. http://dx.doi.org/10.1039/c1ob06697h,2012.
APA	Liu, Xue-Kui,Zheng, Xiao,Ruan, Yuan-Ping,Ma, Jie,Huang, Pei-Qiang,&黄培强.(2012).One-pot reductive coupling of N-acylcarbamates with activated alkenes: application to the asymmetric synthesis of pyrrolo[1,2-a]azepin-5-one ring system and (-)-xenovenine.http://dx.doi.org/10.1039/c1ob06697h.
MLA	Liu, Xue-Kui,et al."One-pot reductive coupling of N-acylcarbamates with activated alkenes: application to the asymmetric synthesis of pyrrolo[1,2-a]azepin-5-one ring system and (-)-xenovenine".http://dx.doi.org/10.1039/c1ob06697h (2012).