Efficient synthesis of a chiral [4]pseudocatenane and its derivatives: A novel ship's wheel-like interlocked structure

doi:10.1002/chem.200600195

CORC > 化学研究所 > 中国科学院化学研究所

	Efficient synthesis of a chiral [4]pseudocatenane and its derivatives: A novel ship's wheel-like interlocked structure
	Zhu, Xiao-Zhang ; Chen, Chuan-Feng
刊名	CHEMISTRY-A EUROPEAN JOURNAL
	2006-07-17
卷号	12 期号:21 页码:5603-5609
关键词	Catenanes Chemical Topology Chirality Reactivity Template Synthesis
ISSN号	0947-6539
DOI	10.1002/chem.200600195
英文摘要	A novel chiral [4]pseudocatenane 5H(3)]PF6](3) was synthesized efficiently by treatment of a solution of chiral tliptycene-based tri(crown ether) 1 and three equivalents of a bis[p-(but-3-enyloxy)benzyl]ammonium salt in CH2Cl2 with a Grubbs II catalyst, followed by hydrogenation. It was found that the ammonium groups in 5H(3)- [PF6](3) could be deprotonated by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) in acetonitrile or dimethyl sulfoxide (DMSO). Consequently, N-acylation of the ammonium groups was easily performed in the presence of DBU, which resulted in a new class of neutral highly ordered interlocked molecules in good yields. In particular, the incorporation of stopper units, for example, diethyl phosphoramidate, lead to the isolation of the interlocked molecule 10 with an interesting ship's wheel-like structure, which was structurally studied with the help of detailed NMR experiments. Compared with 1, it was further found that the Cotton effect of (R)-1,1'-binaphthyl chromophore at 241 nm was greatly reduced in 5H(3)-[PF6](3) and its derivatives. Moreover, a new positive Cotton effect at 248 nm appeared in the interlocked molecules; this observation could be attributed to the chirality transfer from the binaphthyl units to the macrocycles lying in the cavities of 1.
语种	英语
出版者	WILEY-V C H VERLAG GMBH
WOS记录号	WOS:000239325400022
内容类型	期刊论文
源URL	[http://ir.iccas.ac.cn/handle/121111/58717]
专题	中国科学院化学研究所
通讯作者	Chen, Chuan-Feng
作者单位	1.Chinese Acad Sci, Inst Chem, Ctr Mol Sci, Beijing 100080, Peoples R China 2.Chinese Acad Sci, Grad Sch, Beijing 100049, Peoples R China
推荐引用方式 GB/T 7714	Zhu, Xiao-Zhang,Chen, Chuan-Feng. Efficient synthesis of a chiral [4]pseudocatenane and its derivatives: A novel ship's wheel-like interlocked structure[J]. CHEMISTRY-A EUROPEAN JOURNAL,2006,12(21):5603-5609.
APA	Zhu, Xiao-Zhang,&Chen, Chuan-Feng.(2006).Efficient synthesis of a chiral [4]pseudocatenane and its derivatives: A novel ship's wheel-like interlocked structure.CHEMISTRY-A EUROPEAN JOURNAL,12(21),5603-5609.
MLA	Zhu, Xiao-Zhang,et al."Efficient synthesis of a chiral [4]pseudocatenane and its derivatives: A novel ship's wheel-like interlocked structure".CHEMISTRY-A EUROPEAN JOURNAL 12.21(2006):5603-5609.