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Catalyst-Dependent Stereodivergent and Regioselective Synthesis of Indole-Fused Heterocycles through Formal Cycloadditions of Indolyl-Allenes
Alternative Title催化剂调控的从吲哚和联烯的环加成反应高立体和区域选择性地制备含有吲哚的杂环化合物
MEI LIANGYONG1; Wei Y(魏音)1; Tang XY(唐翔鹰)1; Shi M(施敏)1
2015
Source PublicationJ. Am. Chem. Soc.
Volume137Issue:25Pages:8131-8137
AbstractStereo- and regioselective construction of poly-heterocycles, especially those with several contiguous stereocenters, is still a challenge. In this paper, catalyst-dependent stereodivergent and regioselective synthesis of indole-fused heterocycles through formal cycloadditions of indolyl-allenes has been developed. The reaction features total reversion of an all-carbon quaternary stereocenter when a gold or platinum complex was employed as the catalyst through [3 + 2] cycloaddition of allene with indole, affording different diazabenzo[a]cyclopenta[cd]azulenes as epimers, respectively. In addition, in the presence of IPrAuCl and AgNTf2, highly regioselective exo-type [2 + 2] cycloaddition was observed, in which allene served as a 2C synthon. This methodology provides a simple and straightforward approach for the construction of indole-fused tricyclic systems under mild conditions in an atom-economical way.
Subtype论文
Subject Area金属有机化学
DOI10.1021/jacs.5b02080
URL查看原文
Indexed BySCI
Language英语
WOS IDWOS:000357436300033
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Document Type期刊论文
Identifierhttp://ir.sioc.ac.cn/handle/331003/39624
Collection金属有机化学国家重点实验室
Corresponding AuthorTang XY(唐翔鹰); Shi M(施敏)
Affiliation1.中科院上海有机化学研究所, 金属有机化学国家重点实验室
2.华东理工大学
Recommended Citation
GB/T 7714
MEI LIANGYONG,Wei Y,Tang XY,et al. Catalyst-Dependent Stereodivergent and Regioselective Synthesis of Indole-Fused Heterocycles through Formal Cycloadditions of Indolyl-Allenes[J]. J. Am. Chem. Soc.,2015,137(25):8131-8137.
APA MEI LIANGYONG,魏音,唐翔鹰,&施敏.(2015).Catalyst-Dependent Stereodivergent and Regioselective Synthesis of Indole-Fused Heterocycles through Formal Cycloadditions of Indolyl-Allenes.J. Am. Chem. Soc.,137(25),8131-8137.
MLA MEI LIANGYONG,et al."Catalyst-Dependent Stereodivergent and Regioselective Synthesis of Indole-Fused Heterocycles through Formal Cycloadditions of Indolyl-Allenes".J. Am. Chem. Soc. 137.25(2015):8131-8137.
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