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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
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)
2005
发表期刊J. Am. Chem. Soc.
ISSN0002-7863
卷号127期号:26页码:9603-9611
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.
学科领域天然产物有机化学
部门归属上海有机所; 香港中文大学
URL查看原文
收录类别SCI
语种英语
WOS记录号WOS:000230220900063
引用统计
被引频次:86[WOS]   [WOS记录]     [WOS相关记录]
文献类型期刊论文
条目标识符http://ir.sioc.ac.cn/handle/331003/27621
专题上海有机化学研究所
通讯作者Huang NZ(黄乃正)
推荐引用方式
GB/T 7714
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.
APA 彭海燕.,林志强.,麦松威.,蔡忠伟.,马伟强.,...&黄乃正.(2005).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. Am. Chem. Soc.,127(26),9603-9611.
MLA 彭海燕,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. Am. Chem. Soc. 127.26(2005):9603-9611.
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