Synthesis of trisubstituted allenamides utilizing 1,2-rearrangement of dialkoxyphosphoryl moiety under Brønsted base catalysis

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Abstract

A new method for the synthesis of trisubstituted allenamides was developed by utilizing the 1,2-rearrangement of a dialkoxyphosphoryl moiety from carbon to nitrogen under Brønsted base catalysis. The reaction would involve the catalytic generation of an α-amino propargyl anion through the key rearrangement, the addition to an electrophile at the α-position of the anionic intermediate, and the unprecedented rearrangement of a phosphoramidate moiety of the adduct, providing trisubstituted allenamides that are difficult to synthesize by using conventional methods.

Original languageEnglish
Pages (from-to)1164-1167
Number of pages4
JournalChemistry Letters
Volume48
Issue number9
DOIs
Publication statusPublished - 2019 Jan 1

Keywords

  • Allenamides
  • Brønsted base catalysis
  • Rearrangement

ASJC Scopus subject areas

  • Chemistry(all)

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