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

Department of Chemistry

Research output: Contribution to journal › Article

7 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 Jan 1

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ASJC Scopus subject areas

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

Cite this

Chen, Y. R., Ganapuram, M. R., Hsieh, K. H., Chen, K. H., Karanam, P., Vagh, S. S., Liou, Y. C., & Lin, W. (2018). 3-Homoacyl coumarin: An all carbon 1,3-dipole for enantioselective concerted (3+2) cycloaddition. Chemical Communications, 54(90), 12702-12705. https://doi.org/10.1039/c8cc07271j

3-Homoacyl coumarin : An all carbon 1,3-dipole for enantioselective concerted (3+2) cycloaddition. / Chen, Yi Ru; Ganapuram, Madhusudhan Reddy; Hsieh, Kai Hong; Chen, Kai Han; Karanam, Praneeth; Vagh, Sandip Sambhaji; Liou, Yan Cheng; Lin, Wenwei.

In: Chemical Communications, Vol. 54, No. 90, 01.01.2018, p. 12702-12705.

Research output: Contribution to journal › Article

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Access to Document

10.1039/c8cc07271j