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题名: Copper-Catalyzed Formal Carbene Migratory Insertion into Internal Olefinic C=C Bonds with N-Tosylhydrazones To Access Iminofuran and 2(3H)-Furanone Derivatives
作者: Huang, Fei1, 2;  Liu, Zhuqing1, 2;  Wang, Quannan1, 2;  Lou, Jiang1, 2;  Yu, Zhengkun1, 3
刊名: ORGANIC LETTERS
发表日期: 2017-07-07
DOI: 10.1021/acs.orglett.7b01668
卷: 19, 期:13, 页:3660-3663
收录类别: SCI
文章类型: Article
WOS标题词: Science & Technology ;  Physical Sciences
类目[WOS]: Chemistry, Organic
研究领域[WOS]: Chemistry
英文摘要: Efficient copper-catalyzed formal carbene migratory insertion into the olefinic C=C bonds of internal olefins, that is, alpha-oxo ketene N,S-acetals, has been achieved by means of N-tosylhydrazones of ketones as the carbene precursors. Iminofuran derivatives were obtained and further transformed to the corresponding 2(3H)-furanones and 4-oxobutanoates (gamma-ketoesters), respectively, under mild conditions. In a similar fashion, alpha-thioxo ketene N,S-acetals reacted with N-tosylhydrazones of ketones to afford iminothiophenes. It is suggested that formal carbene migratory insertion into the olefinic C=C bond is involved in the overall catalytic cycle, demonstrating a new type of carbene insertion reaction for five-membered heterocycle construction.
关键词[WOS]: C-C BOND ;  DIAZO-COMPOUNDS ;  ENANTIOSELECTIVE INSERTION ;  KETENE N,S-ACETALS ;  H BONDS ;  FUNCTIONALIZATION ;  ACTIVATION ;  CARBON ;  DIAZOESTERS ;  TRANSFORMATIONS
语种: 英语
WOS记录号: WOS:000405358300083
Citation statistics: 
内容类型: 期刊论文
URI标识: http://cas-ir.dicp.ac.cn/handle/321008/152043
Appears in Collections:中国科学院大连化学物理研究所_期刊论文

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作者单位: 1.Chinese Acad Sci, Dalian Inst Chem Phys, 457 Zhongshan Rd, Dalian 116023, Peoples R China
2.Univ Chinese Acad Sci, Beijing 100049, Peoples R China
3.Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, 354 Fenglin Rd, Shanghai 200032, Peoples R China

Recommended Citation:
Huang, Fei,Liu, Zhuqing,Wang, Quannan,et al. Copper-Catalyzed Formal Carbene Migratory Insertion into Internal Olefinic C=C Bonds with N-Tosylhydrazones To Access Iminofuran and 2(3H)-Furanone Derivatives[J]. ORGANIC LETTERS,2017,19(13):3660-3663.
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