Gold(I)-catalyzed heterocyclization of β-alkynyl hydroxamic acids: synthesis of isoxazolidin-3-ones

Gold(I)-catalyzed heterocyclization of β-alkynyl hydroxamic acids: synthesis of isoxazolidin-3-ones

A practical and mild method for the 5- exo cyclization of N-substituted α -alkynyl hydroxamic acids into isoxazolidin-3-ones catalyzed by Au(PPh 3 )SbF 6 was developed. Under optimized conditions, the cyclization shows a high Z -selectivity for the newly formed exocyclic double bond. Graphical Abstr...

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Veröffentlicht in:Monatshefte für Chemie 2015-01, Vol.146 (1), p.119-134
Hauptverfasser: Häring, Andreas P., Klahn, Philipp, Jübermann, Martin, Mohr, Fabian, Kirsch, Stefan F.
Format: Artikel
Sprache:eng
Schlagworte:
Analytical Chemistry
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Inorganic Chemistry
Organic Chemistry
Original Paper
Physical Chemistry
Theoretical and Computational Chemistry
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Zusammenfassung:A practical and mild method for the 5- exo cyclization of N-substituted α -alkynyl hydroxamic acids into isoxazolidin-3-ones catalyzed by Au(PPh 3 )SbF 6 was developed. Under optimized conditions, the cyclization shows a high Z -selectivity for the newly formed exocyclic double bond. Graphical Abstract
ISSN:0026-9247
1434-4475
DOI:10.1007/s00706-014-1319-1