Radical Cyclization of Epoxy Vinyl- and Allylsulfones Promoted by Titanocene Chloride

A titanocene-mediated intramolecular radical addition of different epoxy vinyl- and allylsulfones has been achieved. Five- and six-membered ring products were obtained in good to excellent yields in the presence of both 2.2 and 0.2 equiv of Cp2TiCl. A novel double-activation strategy allowed us to a...

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Bibliographic Details
Published in:Journal of organic chemistry 2015-05, Vol.80 (9), p.4378-4391
Main Authors: Fernández-Mateos, A, Madrazo, S. Encinas, Teijón, P. Herrero, González, R. Rubio
Format: Article
Language:English
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Summary:A titanocene-mediated intramolecular radical addition of different epoxy vinyl- and allylsulfones has been achieved. Five- and six-membered ring products were obtained in good to excellent yields in the presence of both 2.2 and 0.2 equiv of Cp2TiCl. A novel double-activation strategy allowed us to achieve small-size rings such as cyclobutanes and cyclopropanes.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.5b00206