Synthesis of N-acyl-N,O-acetals from N-aryl amides and acetals in the presence of TMSOTf

C. Wade Downey*, Alan S. Fleisher, James T. Rague, Chelsea L. Safran, Megan E. Venable, Robert D. Pike

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Secondary amides undergo in situ silyl imidate formation mediated by TMSOTf and an amine base, followed by addition to acetal acceptors to provide N-acyl-N,O-acetals in good yields. An analogous, high-yielding reaction is observed with 2-mercaptothiazoline as the silyl imidate precursor. Competing reduction of the acetal to the corresponding methyl ether via transfer hydrogenation can be circumvented by the replacement of CY2NMe with 2,6-lutidine under otherwise identical reaction conditions.

Original languageEnglish (US)
Pages (from-to)4756-4759
Number of pages4
JournalTetrahedron Letters
Volume52
Issue number37
DOIs
StatePublished - Sep 14 2011

Keywords

  • N,O-Acetal
  • Silyl imidate
  • Silyl triflate
  • Silyl trifluoromethanesulfonate

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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