Organic Letters 2013-12-20

Tri- and tetrasubstituted functionalized vinyl sulfides by radical allylation.

Laurent Debien, Marie-Gabrielle Braun, Béatrice Quiclet-Sire, Samir Z Zard

Index: Org. Lett. 15(24) , 6250-3, (2013)

Full Text: HTML

Abstract

2-Fluoropyridinyl-6-oxy- precursors derived from phenyl vinyl sulfide react with radicals generated from xanthates via an addition-elimination process to furnish the corresponding vinyl sulfides in good yields. This convergent method is operationally simple and enables a straightforward synthesis of the difficult to access tetrasubstituted vinyl sulfides. Vinyl sulfides were used as more robust enol ether surrogates in highly stereoselective reactions with N-acylium cations leading to nitrogen-containing polycyclic structures.