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Issue 89, 2012
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Tuning efficiency of the 4-exo-trig cyclization by the electronic effect: ring closure of 3,3-difluoro-4-pentenyl carbon radicals and synthesis of a gem-difluorocyclobutane nucleoside

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Abstract

4-exo-trig Cyclization reaction of a 4-pentenyl carbon radical containing the gem-difluoromethylene moiety adjacent to a radical accepting α,β-unsaturated ester was found to proceed efficiently to furnish a novel gem-difluorocyclobutane derivative. The cyclized product could be transformed into a gem-difluoromethylene analogue of oxetanocin T.

Graphical abstract: Tuning efficiency of the 4-exo-trig cyclization by the electronic effect: ring closure of 3,3-difluoro-4-pentenyl carbon radicals and synthesis of a gem-difluorocyclobutane nucleoside

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Publication details

The article was received on 14 Aug 2012, accepted on 20 Sep 2012 and first published on 24 Sep 2012


Article type: Communication
DOI: 10.1039/C2CC35876J
Citation: Chem. Commun., 2012,48, 10993-10995
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    Tuning efficiency of the 4-exo-trig cyclization by the electronic effect: ring closure of 3,3-difluoro-4-pentenyl carbon radicals and synthesis of a gem-difluorocyclobutane nucleoside

    H. Kumamoto, S. Kawahigashi, H. Wakabayashi, T. Nakano, T. Miyaike, Y. Kitagawa, H. Abe, M. Ito, K. Haraguchi, J. Balzarini, M. Baba and H. Tanaka, Chem. Commun., 2012, 48, 10993
    DOI: 10.1039/C2CC35876J

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