Type 2 intramolecular nitroso Diels-Alder reaction. Synthesis and structure of bridgehead oxazinolactams

Authors
Sparks, SM Vargas, JD Shea, KJ
Citation
Sm. Sparks et al., Type 2 intramolecular nitroso Diels-Alder reaction. Synthesis and structure of bridgehead oxazinolactams, ORG LETT, 2(10), 2000, pp. 1473-1475
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
2
Issue
10
Year of publication
2000
Pages
1473 - 1475
Database
ISI
SICI code
1523-7060(20000518)2:10<1473:T2INDR>2.0.ZU;2-M
Abstract
[GRAPHICS] The type 2 intramolecular Diels-Alder cycloaddition utilizing N-acylnitroso dienophiles provides an efficient entry into bridged oxazinolactams. In co ntrast to the bimolecular counterpart, the reaction is completely regiosele ctive, Structural characterization of the cycloadducts allows for evaluatio n of the olefin distortion and the degree of pyramidalization of the bridge head oxazinolactam.