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

• DOI: 10.1002/ejoc.201200513
• Publication Date: 2012-05-31T09:46:47Z
• Authors: Cong S. Vu; Nicolas Guisot; Stéphane Guillarme; Arnaud Martel; Gilles Dujardin; Muriel Pipelier; Didier Dubreuil; Christine Saluzzo
• Keywords: Lactones; Diastereoselectivity; [CHIM.ORGA]Chemical Sciences/Organic chemistry; Asymmetric synthesis; 540; Chiral auxiliaries; 01 natural sciences; Cycloaddition; 0104 chemical sciences

AbstractEu(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.