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学科主题: 天然产物有机化学
题名: Chiral rodlike platinum complexes, double helical chains, and potential asymmetric hydrogenation ligand based on "linear" building blocks: 1,8,9,16-tetrahydroxytetraphenylene and 1,8,9,16-tetrakis(diphenylphosphino)tetraphenylene
其他题名: 手性1,8,9,16-四取代四苯并环辛四烯的合成以及不对称氢化活性研究
作者: Peng HY(彭海燕) ; Lin ZQ(林志强) ; Mai SW(麦松威) ; Cai ZW(蔡忠伟) ; Ma WQ(马伟强) ; Li YX(李玉学) ; Huang NZ(黄乃正)
通讯作者: 黄乃正
刊名: J. Am. Chem. Soc.
发表日期: 2005
卷: 127, 期:26, 页:9603-9611
收录类别: SCI
部门归属: 上海有机所; 香港中文大学
英文摘要: This paper is concerned with the synthesis of 1,8,9,16-tetrahydroxytetraphenylene (3a) via copper(II)-mediated oxidative coupling, its resolution to optical antipodes, and its conversion to 1,8,9,16-tetrakis-(diphenylphosphino)tetraphenylene (3b). On the basis of these chiral "linear" building blocks, three rodlike chiral complexes, triblock (R,R,R,R)-17 and (S,S,S,S)-20 and pentablock (R,R,R,R,R,R,R,R)-22, were constructed. As a hydrogen bond donor, racemic and optically active 3a was allowed to assemble with linear acceptors to afford highly ordered structures. A 1:1 adduct of 4,4'-bipyridyl and (+/-)-3a exists in a dimeric form of 3a linked by 4,4'-bipyridyl through hydrogen bonds. Pyrazine serves as a short linker between achiral parallel chains each formed by (+/-)-3a, while self-assembly of homochiral 3a into alternate parallel chains occurs in the adduct of 5,5'-dipyrimidine with (+/-)-3a. Self-assembly of (S,S)-3a or (R,R)-3a with 4,4'-dipyridyl yielded a packing of chiral double helical chains formed by chiral tetrol 3a molecules. A novel chiral ligand, (S,S)-23, derived from 3a was used in the asymmetric catalytic hydrogenation of alpha-acetamidocinnamate, yielding up to 99.0% ee and 100% conversion.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000230220900063
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/27621
Appears in Collections:上海有机化学研究所_期刊论文

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Recommended Citation:
Peng HY,Lin ZQ,Mai SW,et al. Chiral rodlike platinum complexes, double helical chains, and potential asymmetric hydrogenation ligand based on "linear" building blocks: 1,8,9,16-tetrahydroxytetraphenylene and 1,8,9,16-tetrakis(diphenylphosphino)tetraphenylene[J]. J. Am. Chem. Soc.,2005,127(26):9603-9611.
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