期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2017, 期 22, 页码 3265-3273出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201700472
关键词
Amino acids; Isoxazolidinones; Heterocycles; Meldrum's acid; Reduction; Multicomponent reactions
资金
- INSA Rouen, Rouen University, the Centre National de la Recherche Scientifique (CNRS)
- EFRD
- Labex SynOrg [ANR-11-LABX-0029]
- Region Normandie (CRUNCh network)
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 un-precedented N-Fmoc-isoxazolidin-5-ones. Subsequent chemo-selective 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.
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