A Convergent Hetero-Diels-Alder Strategy for Asymmetric Access to a Lactone Containing Two Lipidic Chains

Cong Sau Vu (1) , Nicolas Guisot (1) , Stéphane Guillarme (1) , Arnaud Martel (1) , Gilles Dujardin (1) , Muriel Pipelier (2) , Didier Dubreuil (2) , Christine Saluzzo (1)

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

Eu(fod)3-catalyzed heterocycloaddition of chiral β-alkyl-N-vinyl-1,3-oxazolidin-2-ones with a heterodiene bearing a lipidic chain led to heterocycloadducts in high yield with excellent endo and facial selectivities. An original lipidic lactone, a potent precursor of a ceramide analog, was obtained in seven steps from the adduct in a convergent manner after appropriate functionalization.

Mots clés: Lactones; Asymmetric synthesis; Chiral auxiliaries; Cycloaddition; Diastereoselectivity

Domaines: Chimie organique

Cong Sau Vu, Nicolas Guisot, Stéphane Guillarme, Arnaud Martel, Gilles Dujardin, et al.. A Convergent Hetero-Diels-Alder Strategy for Asymmetric Access to a Lactone Containing Two Lipidic Chains. European Journal of Organic Chemistry, 2012, 2012 (20), pp.3703-3870. ⟨10.1002/ejoc.201200513⟩. ⟨hal-00716070⟩