A Meldrum's Acid Based Multicomponent Synthesis of N‐Fmoc‐isoxazolidin‐5‐ones: Entry to N‐Fmoc‐β‐amino Acids. Issue 22 (14th June 2017)

• Record Type: Journal Article
• Authors: Le Foll Devaux, Alexandra; Deau, Emmanuel; Corrot, Emilie; Bischoff, Laurent; Levacher, Vincent; Brière, Jean‐François
• Is Part Of: European journal of organic chemistry. Issue 22(2017)
• Page Start: 3265
• Page End: 3273
• Publication Date: 2017-06-14
• Subjects: Amino acids -- Isoxazolidinones -- Heterocycles -- Meldrum's acid -- Reduction -- Multicomponent reactions; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201700472
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : 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. Abstract : Newly developed conditions allowed a multicomponent KaMC reaction to take place to give previously undescribed N ‐Fmoc‐isoxazolidinones. This led to a two‐step synthesis of N ‐Fmoc‐β 3 ‐amino acid analogues of the proteinogenic amino acids.