Synthesis of Decahydropyrrolo[2,1,5-cd]indolizine through Consecutive   [2+3] Cycloadditions and 6-Exo-Trig Cyclization

doi:10.1021/jo200601y

CORC > 北京大学 > 化学与分子工程学院

	Synthesis of Decahydropyrrolo[2,1,5-cd]indolizine through Consecutive [2+3] Cycloadditions and 6-Exo-Trig Cyclization
	Cui, Peipei ; Xu, Liang ; Shi, Zhangjie ; Gan, Liangbing
刊名	journal of organic chemistry
	2011
关键词	DIMETHYL ACETYLENEDICARBOXYLATE DERIVATIVES ALKALOIDS MALEIMIDES ESTER
DOI	10.1021/jo200601y
英文摘要	Azomethine ylide formed from glycine methyl ester and cinnamaldehyde adds to N-phenylmaleimide to form pyrrolidine derivative, further treatment of which with cinnamaldehyde and N-phenylmaleimide affords the second [2 + 3] cycloaddition adduct, a pyrrolizine derivative with two styrenyl groups at the 3,5-positions. Addition of ICl to the pyrrolizine derivative results in the 6-exo-trig cyclization of the styrenyl groups to form a cycl[3.2.2]azine derivative. The reactions are highly stereoselective affording 11 chiral carbons in three steps. The structure of the cycl[3.2.2]azine derivative was determined by single-crystal X-ray analysis.; http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000290465700074&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=8e1609b174ce4e31116a60747a720701 ; Chemistry, Organic; SCI(E); EI; PubMed; 18; ARTICLE; 10; 4210-4212; 76
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/149981]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Cui, Peipei,Xu, Liang,Shi, Zhangjie,et al. Synthesis of Decahydropyrrolo[2,1,5-cd]indolizine through Consecutive [2+3] Cycloadditions and 6-Exo-Trig Cyclization[J]. journal of organic chemistry,2011.
APA	Cui, Peipei,Xu, Liang,Shi, Zhangjie,&Gan, Liangbing.(2011).Synthesis of Decahydropyrrolo[2,1,5-cd]indolizine through Consecutive [2+3] Cycloadditions and 6-Exo-Trig Cyclization.journal of organic chemistry.
MLA	Cui, Peipei,et al."Synthesis of Decahydropyrrolo[2,1,5-cd]indolizine through Consecutive [2+3] Cycloadditions and 6-Exo-Trig Cyclization".journal of organic chemistry (2011).