A Meldrum's Acid Based Multicomponent Synthesis of N-Fmoc-isoxazolidin-5-ones: Entry to N-Fmoc-[beta]-amino Acids

A Meldrum's Acid Based Multicomponent Synthesis of N-Fmoc-isoxazolidin-5-ones: Entry to N-Fmoc-[beta]-amino Acids

A multicomponent Knoevenagel-aza-Michael cyclocondensation (KaMC) reaction starting from Meldrum's acid has been developed with base-sensitive N-Fmoc-hydroxylamine. The reaction takes place under very mild basic conditions, providing a straightforward synthetic route to various unprecedented N-...

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Veröffentlicht in:European journal of organic chemistry 2017-06, Vol.2017 (22), p.3265
Hauptverfasser: Le Foll Devaux, Alexandra, Deau, Emmanuel, Corrot, Emilie, Bischoff, Laurent, Levacher, Vincent, Briere, Jean-François
Format: Artikel
Sprache:eng
Schlagworte:
Amino acids
Cleavage
Synthesis
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Zusammenfassung:A multicomponent Knoevenagel-aza-Michael cyclocondensation (KaMC) reaction starting from Meldrum's acid has been developed with base-sensitive N-Fmoc-hydroxylamine. The reaction takes place under very mild basic conditions, providing a straightforward synthetic route to various unprecedented N-Fmoc-isoxazolidin-5-ones. Subsequent chemoselective reductive cleavage of the N-O bond in the presence of Zn/AcOH allowed a short synthesis of the corresponding N-Fmoc-[beta]-amino acids.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201700472