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A Convergent Hetero‐Diels–Alder Strategy for Asymmetric Access to a Lactone Containing Two Lipidic Chains
Author(s) -
Vu Cong S.,
Guisot Nicolas,
Guillarme Stéphane,
Martel Arnaud,
Dujardin Gilles,
Pipelier Muriel,
Dubreuil Didier,
Saluzzo Christine
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200513
Subject(s) - chemistry , lactone , adduct , yield (engineering) , alkyl , diels–alder reaction , ceramide , surface modification , organic chemistry , catalysis , stereochemistry , biochemistry , apoptosis , materials science , metallurgy
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.