Selective synthesis of multiply substituted 7-norbornenone derivatives   or Diels-Alder cycloadducts from 1,2,3,4-tetrasubstituted 1,3-butadienes   and maleic anhydride with or without Lewis acids

doi:10.1016/j.tet.2008.08.006

CORC > 北京大学 > 化学与分子工程学院

	Selective synthesis of multiply substituted 7-norbornenone derivatives or Diels-Alder cycloadducts from 1,2,3,4-tetrasubstituted 1,3-butadienes and maleic anhydride with or without Lewis acids
	Li, Dongzhen ; Shi, An ; Zhang, Wen-Xiong ; Liu, Guangzhen ; Xi, Zhenfeng
刊名	tetrahedron
	2008
关键词	PALLADIUM-CATALYZED CYANOESTERIFICATION ALDER/CROSS-COUPLING REACTIONS METAL-PROMOTED CYCLIZATION PI-FACIAL SELECTIVITIES ORGANIC-SYNTHESIS NUCLEOPHILIC ADDITIONS CONJUGATED DIENES CONVENIENT METHOD BOND-CLEAVAGE TANDEM
DOI	10.1016/j.tet.2008.08.006
英文摘要	Reactions of 1,2,3,4-tetrasubstituted 1,3-butadienes with maleic anhydride and other dienophiles were investigated with or without addition of Lewis acid. When the silylated 1,3-butadienes, such as 1,4-bis(trimethylsilyl)-1,3-butadienes or 1-trimethylsilyl-1,3-butadienes, were treated with maleic anhydride in the presence of 2 equiv of AlCl(3), multi-substituted 7-norbomenones of well-defined exo,exo-disubstituted patterns were produced by an unprecedented and synthetically useful tandem process. Although some tetrasubstituted 1,3-butadienes could react directly with maleic anhydride under relative harsh conditions to afford Diels-Alder cycloadducts, the reactions, in the presence of 1 equiv of AlCl(3), afforded the corresponding cycloadducts in higher yields under mild conditions. These results showed that the size and substitution pattern of substituents on the butadienyl skeleton played a very important role in the reactivity of butadienes as a partner for the Diels-Alder reaction and Lewis acid could promote and/or realize the process of a Diels-Alder reaction. (C) 2008 Elsevier Ltd. All rights reserved.; http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=PARTNER_APP&SrcAuth=LinksAMR&KeyUT=WOS:000259939000012&DestLinkType=FullRecord&DestApp=ALL_WOS&UsrCustomerID=8e1609b174ce4e31116a60747a720701 ; Chemistry, Organic; SCI(E); 7; ARTICLE; 42; 9895-9900; 64
语种	英语
内容类型	期刊论文
源URL	[http://ir.pku.edu.cn/handle/20.500.11897/248212]
专题	化学与分子工程学院
推荐引用方式 GB/T 7714	Li, Dongzhen,Shi, An,Zhang, Wen-Xiong,et al. Selective synthesis of multiply substituted 7-norbornenone derivatives or Diels-Alder cycloadducts from 1,2,3,4-tetrasubstituted 1,3-butadienes and maleic anhydride with or without Lewis acids[J]. tetrahedron,2008.
APA	Li, Dongzhen,Shi, An,Zhang, Wen-Xiong,Liu, Guangzhen,&Xi, Zhenfeng.(2008).Selective synthesis of multiply substituted 7-norbornenone derivatives or Diels-Alder cycloadducts from 1,2,3,4-tetrasubstituted 1,3-butadienes and maleic anhydride with or without Lewis acids.tetrahedron.
MLA	Li, Dongzhen,et al."Selective synthesis of multiply substituted 7-norbornenone derivatives or Diels-Alder cycloadducts from 1,2,3,4-tetrasubstituted 1,3-butadienes and maleic anhydride with or without Lewis acids".tetrahedron (2008).