Type 2 intramolecular N-acylnitroso diels-alder reaction: stereoselective synthesis of bridged bicyclic oxazinolactams.
[reaction: see text] The type 2 intramolecular N-acylnitroso Diels-Alder reaction has been employed for the synthesis of substituted bridged bicyclic oxazinolactams. Upon oxidation of hydroxamic acid 6, a 3-benzylated oxazinolactam (7) was synthesized with complete diastereoselectivity. Elaboration of cycloadduct 7 liberated a cis-3,7-disubstituted azocin-2-one (9).
Chow
Chun P
CP
Department of Chemistry, 516 Rowland Hall, University of California, Irvine 92697-2025, USA.
Shea
Kenneth J
KJ
Sparks
Steven M
SM
D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D009603:Nitroso Compounds / Q000737:chemistry*; D013237:Stereoisomerism
D007769:Lactams; D009603:Nitroso Compounds