Type 2 Intramolecular N-Acylnitroso Diels−Alder Reaction: Stereoselective Synthesis of Bridged Bicyclic Oxazinolactams

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 libe...

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Veröffentlicht in:	Organic letters 2002-08, Vol.4 (16), p.2637-2640
Hauptverfasser:	Chow, Chun P, Shea, Kenneth J, Sparks, Steven M
Format:	Artikel
Sprache:	eng
Schlagworte:	Lactams - chemical synthesis Lactams - chemistry Nitroso Compounds - chemistry Stereoisomerism
Online-Zugang:	Volltext
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Zusammenfassung:	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).
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol026075k