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Regioselective Ene-Type Allylic Chlorination of Electron-Rich Alkenes by Activated DMSO

Vera P. Demertzidou, Stavroula Pappa, Vasiliki Sarli and Alexandros L. Zografos*

*Laboratory of Organic Chemistry, Department of Chemistry, Aristotle University of Thessaloniki, Main University Campus, 54124 Thessaloniki, Greece, Email: alzografchem.auth.gr

V. P. Demertzidou, S. Pappa, V. Sarli, A. L. Zografos, J. Org. Chem., 2017, 82, 8710-8715.

DOI: 10.1021/acs.joc.7b01103 (free Supporting Information)


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Abstract

A versatile and scalable protocol involving the activation of DMSO by chlorotrimethysilane enables a chemoselective chlorination of polyprenoids. This simple protocol provides an alternative to existing routes for accessing useful synthetic precursors of complex terpenoids.


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proposed mechanism



Key Words

allylic chlorination, Alder-Ene Reaction


ID: J42-Y2017