Modular approach to saturated and a,ß-unsaturated ketones

Laurent Debien (1) , Béatrice Quiclet-Sire (1) , Samir Z. Zard (1)

1 DCSO - Laboratoire de synthèse organique

2-Fluoro-6-pyridinyloxy derivatives of 2-ethoxyvinyl carbinols react with radicals derived from xanthates by an addition-fragmentation pathway to give highly functionalized ketones after acid hydrolysis. 1,4-Diketones are readily accessible by this approach. a,ß-Unsaturated ketones can be obtained by starting with geminal acetoxy xanthates prepared by addition of a simpler xanthate to vinyl acetate. © 2011 American Chemical Society.

Domains: Chemical Sciences; Organic chemistry

Laurent Debien, Béatrice Quiclet-Sire, Samir Z. Zard. Modular approach to saturated and a,ß-unsaturated ketones. Organic Letters, 2011, 13 (20), pp.5676-5679. ⟨10.1021/ol202399c⟩. ⟨hal-00951228⟩