Generation and hydrolysis of N-acyloxazolinium salts allowing regiospecific acylation of chiral amino alcohols

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Abstract

In an attempt to form 2-alkylidene-1,3-oxazolidines, chiral 2-oxazolines have been N-alkylated and N-acylated. Two new N-methyloxazolinium salts have been prepared and characterised but base treatment resulted in their decomposition. In contrast, attempts to isolate three N-benzoyloxazolinium salts gave the products of their ring hydrolysis: unsymmetrically diacylated amino alcohols whose structure was confirmed by x-ray diffraction in one case. Overall the method allows stepwise regiospecific N,O-diacylation of 1,2-amino alcohols.
Original languageEnglish
Pages (from-to)611-614
Number of pages4
JournalChemistry of Heterocyclic Compounds
Volume56
Issue number5
Early online date2 Jun 2020
DOIs
Publication statusPublished - 15 Jun 2020

Keywords

  • Amino alcohols
  • Acylation
  • Oxazolines
  • Oxazolinium salts
  • Hydrolysis

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