α−Triethylsilyl-α-diazoacetone in double cross-aldolisation: convenient acetone equivalent toward 5-hydroxy-1,3 diketones

Anthony Lancou (1) , Heloua Haroun (1) , Uday K. Kundu (1) , Frédéric Legros (1) , Nicolas Zimmermann (2) , Monique Mathé-Allainmat (2) , Jacques Lebreton (2) , Gilles Dujardin (1) , Catherine Gaulon-Nourry (1) , Pascal Gosselin (1)

1 IMMM - Institut des Molécules et Matériaux du Mans
2 CEISAM - Chimie Et Interdisciplinarité : Synthèse, Analyse, Modélisation

α-Triethylsilyl-α-diazoacetone underwent a sequential aldolisation–deprotection–aldolisation process to access the 2-diazo-3-oxo-1,5-dihydroxy skeleton with significant diversity. The diazo group could be efficiently removed by treatment with rhodium acetate to afford the corresponding 5-hydroxy-1,3-diketones.

Mots clés: Diazoacetone; silyl-protected diazoactone; aldolisation; dediazotation; rhodium acetate

Domaines: Chimie organique

Anthony Lancou, Heloua Haroun, Uday K. Kundu, Frédéric Legros, Nicolas Zimmermann, et al.. α−Triethylsilyl-α-diazoacetone in double cross-aldolisation: convenient acetone equivalent toward 5-hydroxy-1,3 diketones. Tetrahedron, 2012, 68 (47), pp.9652-9657. ⟨10.1016/j.tet.2012.09.063⟩. ⟨hal-00752103⟩