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

作者:Devaux Alexandra Le Foll; Deau Emmanuel; Corrot Emilie; Bischoff Laurent; Levacher Vincent; Briere Jean Francois*
来源:European Journal of Organic Chemistry, 2017, 2017(22): 3265-3273.
DOI:10.1002/ejoc.201700472

摘要

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.

  • 出版日期2017-6-16