Lewis Acid Catalyzed Cascade Reactions of 1,6-Diynes and 1,6-Enynes with Vinylidenecyclopropanes

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	Lewis Acid Catalyzed Cascade Reactions of 1,6-Diynes and 1,6-Enynes with Vinylidenecyclopropanes
	Yao LF(姚梁峰) ; Shi M(施敏)
刊名	Chem.-Eur. J.
	2009
卷号	15 期号:15 页码:3875-3881
其他题名	Lewis酸催化的1,6-双炔以及1,6-双烯炔和亚乙烯基环丙烷的开环反应
通讯作者	施敏
英文摘要	Lewis acid catalyzed reactions of N-(4-hydroxy-4,4-diarylbut-2ynyl)-4-methyl-N-prop-2-ynylbenzene-sulfonam ides or 1,1-diphenyl-4-prop-2-ynyloxybut-2-yn-1-ol (1,6-diynes) 1 and N-allyl-N-(4-hydroxy-4,4-diarylbut-2-ynyl)-4-methylbenzenesulfonamides (1,6-enynes) 2 with vinylidenecyclopropanes 3 selectively produce polycyclic compounds 4, 5 and 10 as well as isopropylidene-3,3-diarylcyclobut-1-enyl-methyl derivatives 6 or 7 in good to high yields depending on the substituents on the benzene ring of 3 under mild conditions. An interesting PtCl2-catalyzed cyclization of 6 and a Cu-(OAc)(2)center dot H2O catalyzed Eglinton coupling reaction of 5 and 10 to produce the corresponding 5-isopropylidenc-6-methyl-1-(toluene-4-sulfonyl)-7-vinyl-1,2,3,4,5,8-hex ahydroazocine derivatives 8 and the coupling products 9 and 11 in good yields have been disclosed, respectively. Plausible mechanisms of these processes have been proposed that belong to a cascade rearrangement followed by the Friedel-Crafts reaction, an intramolecular proton transferring and a cyclization reaction.
学科主题	金属有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1002/chem.200802284
语种	英语
WOS记录号	WOS:000265162900029
公开日期	2013-01-09
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/10294]
专题	上海有机化学研究所_金属有机化学国家重点实验室
推荐引用方式 GB/T 7714	Yao LF,Shi M. Lewis Acid Catalyzed Cascade Reactions of 1,6-Diynes and 1,6-Enynes with Vinylidenecyclopropanes[J]. Chem.-Eur. J.,2009,15(15):3875-3881.
APA	Yao LF,&Shi M.(2009).Lewis Acid Catalyzed Cascade Reactions of 1,6-Diynes and 1,6-Enynes with Vinylidenecyclopropanes.Chem.-Eur. J.,15(15),3875-3881.
MLA	Yao LF,et al."Lewis Acid Catalyzed Cascade Reactions of 1,6-Diynes and 1,6-Enynes with Vinylidenecyclopropanes".Chem.-Eur. J. 15.15(2009):3875-3881.