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^*

^*Corresponding author for this work

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

33 Citations (Scopus)

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.

Original language	English
Pages (from-to)	12702-12705
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	90
DOIs	https://doi.org/10.1039/c8cc07271j
Publication status	Published - 2018

ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
General Chemistry
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/c8cc07271j

Cite this

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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",

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year = "2018",

doi = "10.1039/c8cc07271j",

language = "English",

volume = "54",

pages = "12702--12705",

journal = "Chemical Communications",

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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

PY - 2018

Y1 - 2018

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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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JF - Chemical Communications

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ER -

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

Abstract

ASJC Scopus subject areas

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CCDC 1484301: Experimental Crystal Structure Determination

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

Abstract

ASJC Scopus subject areas

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Datasets

CCDC 1484301: Experimental Crystal Structure Determination

Cite this