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A Meldrum's Acid Based Multicomponent Synthesis of N ‐Fmoc‐isoxazolidin‐5‐ones: Entry to N ‐Fmoc‐β‐amino Acids
Author(s) -
Le Foll Devaux Alexandra,
Deau Emmanuel,
Corrot Emilie,
Bischoff Laurent,
Levacher Vincent,
Brière JeanFrançois
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201700472
Subject(s) - chemistry , meldrum's acid , hydroxylamine , knoevenagel condensation , combinatorial chemistry , cleavage (geology) , organic chemistry , base (topology) , amino acid , reaction conditions , catalysis , mathematical analysis , biochemistry , geotechnical engineering , mathematics , fracture (geology) , engineering
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‐β‐amino acids.