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Issue 90, 2018
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3-Homoacyl coumarin: an all carbon 1,3-dipole for enantioselective concerted (3+2) cycloaddition

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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.

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

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Publication details

The article was received on 07 Sep 2018, accepted on 17 Oct 2018 and first published on 17 Oct 2018


Article type: Communication
DOI: 10.1039/C8CC07271J
Citation: Chem. Commun., 2018,54, 12702-12705
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    3-Homoacyl coumarin: an all carbon 1,3-dipole for enantioselective concerted (3+2) cycloaddition

    Y. Chen, M. R. Ganapuram, K. Hsieh, K. Chen, P. Karanam, S. S. Vagh, Y. Liou and W. Lin, Chem. Commun., 2018, 54, 12702
    DOI: 10.1039/C8CC07271J

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