Iridium-Catalyzed Allylic Vinylation and Asymmetric Allylic Amination Reactions with o-Aminostyrenes

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	Iridium-Catalyzed Allylic Vinylation and Asymmetric Allylic Amination Reactions with o-Aminostyrenes
	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)
刊名	J. Am. Chem. Soc.
	2011
卷号	133 期号:46 页码:19006-19014
ISSN号	0002-7863
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
通讯作者	游书力
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.
学科主题	金属有机化学
收录类别	SCI
原文出处	http://dx.doi.org/10.1021/ja2092954
语种	英语
WOS记录号	WOS:000297398900072
公开日期	2013-02-19
内容类型	期刊论文
源URL	[http://202.127.28.38/handle/331003/16021]
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	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.
APA	叶克印,贺虎,刘文博,戴立信,HELMCHEN GUENTER,&游书力.(2011).Iridium-Catalyzed Allylic Vinylation and Asymmetric Allylic Amination Reactions with o-Aminostyrenes.J. Am. Chem. Soc.,133(46),19006-19014.
MLA	叶克印,et al."Iridium-Catalyzed Allylic Vinylation and Asymmetric Allylic Amination Reactions with o-Aminostyrenes".J. Am. Chem. Soc. 133.46(2011):19006-19014.