A simple method removing 2-oxazolidinone and 2-hydroxyethylamine auxiliaries in methoxide-carbonate systems for synthesis of planar-chiral nicotinate

Nobuhiro Kanomata, Satoshi Maruyama, Katsuhito Tomono, Shinnosuke Anada

Research output: Contribution to journalArticle

27 Citations (Scopus)

Abstract

A facile and practical removal of 2-oxazolidinone and 2-hydroxyethylamine auxiliaries was accomplished by treating the corresponding N-acyl-2-oxazolidinone and N-(2-hydroxyethyl)amide derivatives in simple methoxide-carbonate systems. The presence of excess DMC (dimethyl carbonate) accelerates the N-acyl bond cleavage for those substrates under mild reaction conditions, and the present method was found to be useful especially for the synthesis of planar-chiral nicotinate.

Original languageEnglish
Pages (from-to)3599-3603
Number of pages5
JournalTetrahedron Letters
Volume44
Issue number18
DOIs
Publication statusPublished - 2003 Apr 28
Externally publishedYes

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Oxazolidinones
Niacin
Carbonates
Amides
Derivatives
Substrates
methyl carbonate

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

A simple method removing 2-oxazolidinone and 2-hydroxyethylamine auxiliaries in methoxide-carbonate systems for synthesis of planar-chiral nicotinate. / Kanomata, Nobuhiro; Maruyama, Satoshi; Tomono, Katsuhito; Anada, Shinnosuke.

In: Tetrahedron Letters, Vol. 44, No. 18, 28.04.2003, p. 3599-3603.

Research output: Contribution to journalArticle

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