A short access to 3,5-disubstituted piperazinones based on the aza-Michael addition of α-amino esters to β-substituted nitroalkenes

Takayuki Kudoh, Seiji Isoyama, Sachiko Kagimoto, Katsutoshi Kurihara, Akira Sakakura

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

A simple procedure for the synthesis of chiral 3,5-disubstituted piperazinones is described. The aza-Michael addition of α-amino esters to β-substituted nitroalkenes in an organic/aqueous biphasic solvent system followed by reduction of a nitro group with zinc nanopowder in acidic media and intramolecular ester–amide exchange under heating conditions gives piperazinones in good overall yields. This novel three-step process can provide a short access to a variety of chiral 3,5-disubstituted piperazinones simply by changing the combination of starting nitroalkenes and α-amino esters. This process can be applied to the concise synthesis of the piperazinone-containing natural product 6′,6″-didebromo-cis-3,4-dihydrohamacanthin B.

Original languageEnglish
Pages (from-to)4693-4696
Number of pages4
JournalTetrahedron Letters
Volume57
Issue number42
DOIs
Publication statusPublished - Oct 19 2016

Keywords

  • 6′,6″-Didebromo-cis-3,4-dihydrohamacanthin B
  • Aza-Michael addition
  • Piperazinone
  • α-Amino ester
  • β-Substituted nitroalkene

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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