Combining Two-Directional Synthesis and Tandem Reactions, Part 8: A Novel Condensation/Michael Addition/Cycloaddition/Fragmentation/Lactamisation Cascade

Combining Two-Directional Synthesis and Tandem Reactions, Part 8: A Novel Condensation/Michael Addition/Cycloaddition/Fragmentation/Lactamisation Cascade

Abstract A tandem oxime formation/Michael addition/1,4-prototopic shift/[3+2]-cycloaddition of an acyclic symmetrical precursor results in a tricyclic isooxazolidine which then undergoes a further fragmentation/lactamisation cascade to generate a non-symmetrical tricyclic a-ketolactam as a single di...

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Veröffentlicht in:Synlett 2006-09, Vol.2006 (14), p.2321-2324
Hauptverfasser: Sinclair, Alex, Arini, Louise G., Rejzek, Martin, Szeto, Peter, Stockman, Robert A.
Format: Artikel
Sprache:eng
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cluster
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Zusammenfassung:Abstract A tandem oxime formation/Michael addition/1,4-prototopic shift/[3+2]-cycloaddition of an acyclic symmetrical precursor results in a tricyclic isooxazolidine which then undergoes a further fragmentation/lactamisation cascade to generate a non-symmetrical tricyclic a-ketolactam as a single diastereomer.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-2006-949634