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学科主题: 金属有机化学
题名: Iridium-Catalyzed Allylic Vinylation and Asymmetric Allylic Amination Reactions with o-Aminostyrenes
其他题名: 铱催化的邻氨基苯乙烯的烯丙基烯基化和不对称烯丙基胺化反应
作者: Ye KY(叶克印) ; He H(贺虎) ; Liu WB(刘文博) ; Dai LX(戴立信) ; HELMCHEN GUENTER ; You SL(游书力)
通讯作者: 游书力
刊名: J. Am. Chem. Soc.
发表日期: 2011
卷: 133, 期:46, 页:19006-19014
收录类别: SCI
部门归属: 中科院上海有机化学研究所; 海德堡大学
英文摘要: An Ir-catalyzed allylic vinylation reaction of allyl carbonates with o-aminostyrene derivatives has been realized, providing skipped (Z,E)-diene derivatives. With (E)-but-2-ene-1,4-diyl dimethyl dicarbonate as the substrate, an efficient enantioselective synthesis of 1-benzazepine derivatives via an Ir-catalyzed domino allylic vinylation/intramolecular allylic amination reaction has been developed. Mechanistic studies of the allylic vinylation reaction have been carried out, and the results suggest that the leaving group of the allylic precursor plays a key role in directing the reaction pathway. Screening of various allylic precursors showed that Ir-catalyzed reactions of allyl diethyl phosphates with o-aminostyrene derivatives proceed via an allylic animation pathway. A subsequent ring-closing metathesis (RCM) reaction of the amination products led to a series of enantiomerically enriched 1,2-dihydroquinoline derivatives. Their utility is indicated by an asymmetric total synthesis of (-)-angustureine.
语种: 英语
相关网址: 查看原文
WOS记录号: WOS:000297398900072
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内容类型: 期刊论文
URI标识: http://ir.sioc.ac.cn/handle/331003/16021
Appears in Collections:金属有机化学国家重点实验室_期刊论文

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Recommended Citation:
Ye KY,He H,Liu WB,et al. Iridium-Catalyzed Allylic Vinylation and Asymmetric Allylic Amination Reactions with o-Aminostyrenes[J]. J. Am. Chem. Soc.,2011,133(46):19006-19014.
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