3-Homoacyl coumarin: An all carbon 1,3-dipole for enantioselective concerted (3+2) cycloaddition

Yi Ru Chen; Madhusudhan Reddy Ganapuram; Kai Hong Hsieh; Kai Han Chen; Praneeth Karanam; Sandip Sambhaji Vagh; Yan Cheng Liou; Wenwei Lin

doi:10.1039/c8cc07271j

3-Homoacyl coumarin: An all carbon 1,3-dipole for enantioselective concerted (3+2) cycloaddition

Yi Ru Chen, Madhusudhan Reddy Ganapuram, Kai Hong Hsieh, Kai Han Chen, Praneeth Karanam, Sandip Sambhaji Vagh, Yan Cheng Liou, Wenwei Lin^*

^*此作品的通信作者

化學系

研究成果: 雜誌貢獻 › 期刊論文 › 同行評審

29 引文斯高帕斯（Scopus）

摘要

A new type of all-carbon 1,3-dipole precursor, 3-homoacylcoumarin, was employed for the stereoselective (3+2) cycloaddition with indandione alkylidenes to generate a series of coumarin/indandione-fused spirocyclopentanes bearing four contiguous stereogenic centers. While two reaction pathways progressed simultaneously, detailed mechanistic investigation revealed that the highly efficient stereoselective concerted route dominated the extremely slow stepwise pathway.

原文	英語
頁（從 - 到）	12702-12705
頁數	4
期刊	Chemical Communications
卷	54
發行號	90
DOIs	https://doi.org/10.1039/c8cc07271j
出版狀態	已發佈 - 2018

ASJC Scopus subject areas

催化
電子、光磁材料
陶瓷和複合材料
化學 (全部)
表面、塗料和薄膜
金屬和合金
材料化學

存取文件

10.1039/c8cc07271j

其它文件與鏈接

CCDC 1484301: Experimental Crystal Structure Determination
Chen, Y. (Creator), Ganapuram, M. R. (Creator), Hsieh, K. (Creator), Chen, K. (Creator), Karanam, P. (Creator), Vagh, S. S. (Creator), Liou, Y. (Creator) & Lin, W. (Creator), Unknown Publisher, 2018
DOI: 10.5517/ccdc.csd.cc1ltjpm, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/ccdc.csd.cc1ltjpm&sid=DataCite
資料集: Dataset

引用此

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title = "3-Homoacyl coumarin: An all carbon 1,3-dipole for enantioselective concerted (3+2) cycloaddition",

abstract = "A new type of all-carbon 1,3-dipole precursor, 3-homoacylcoumarin, was employed for the stereoselective (3+2) cycloaddition with indandione alkylidenes to generate a series of coumarin/indandione-fused spirocyclopentanes bearing four contiguous stereogenic centers. While two reaction pathways progressed simultaneously, detailed mechanistic investigation revealed that the highly efficient stereoselective concerted route dominated the extremely slow stepwise pathway.",

author = "Chen, {Yi Ru} and Ganapuram, {Madhusudhan Reddy} and Hsieh, {Kai Hong} and Chen, {Kai Han} and Praneeth Karanam and Vagh, {Sandip Sambhaji} and Liou, {Yan Cheng} and Wenwei Lin",

note = "Funding Information: The authors thank the Ministry of Science and Technology of the Republic of China (MOST 104-2113-M-003-002-MY3) for financial support. Publisher Copyright: {\textcopyright} 2018 The Royal Society of Chemistry.",

year = "2018",

doi = "10.1039/c8cc07271j",

language = "English",

volume = "54",

pages = "12702--12705",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

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T1 - 3-Homoacyl coumarin

T2 - An all carbon 1,3-dipole for enantioselective concerted (3+2) cycloaddition

AU - Chen, Yi Ru

AU - Ganapuram, Madhusudhan Reddy

AU - Hsieh, Kai Hong

AU - Chen, Kai Han

AU - Karanam, Praneeth

AU - Vagh, Sandip Sambhaji

AU - Liou, Yan Cheng

AU - Lin, Wenwei

N1 - Funding Information: The authors thank the Ministry of Science and Technology of the Republic of China (MOST 104-2113-M-003-002-MY3) for financial support. Publisher Copyright: © 2018 The Royal Society of Chemistry.

PY - 2018

Y1 - 2018

N2 - A new type of all-carbon 1,3-dipole precursor, 3-homoacylcoumarin, was employed for the stereoselective (3+2) cycloaddition with indandione alkylidenes to generate a series of coumarin/indandione-fused spirocyclopentanes bearing four contiguous stereogenic centers. While two reaction pathways progressed simultaneously, detailed mechanistic investigation revealed that the highly efficient stereoselective concerted route dominated the extremely slow stepwise pathway.

AB - A new type of all-carbon 1,3-dipole precursor, 3-homoacylcoumarin, was employed for the stereoselective (3+2) cycloaddition with indandione alkylidenes to generate a series of coumarin/indandione-fused spirocyclopentanes bearing four contiguous stereogenic centers. While two reaction pathways progressed simultaneously, detailed mechanistic investigation revealed that the highly efficient stereoselective concerted route dominated the extremely slow stepwise pathway.

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JO - Chemical Communications

JF - Chemical Communications

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IS - 90

ER -

3-Homoacyl coumarin: An all carbon 1,3-dipole for enantioselective concerted (3+2) cycloaddition

摘要

ASJC Scopus subject areas

存取文件

其它文件與鏈接

指紋

資料集

CCDC 1484301: Experimental Crystal Structure Determination

引用此