N-carbamylamino alcohols as the precursors of oxazolidinones via nitrosation-deamination reaction

Masumi Suzuki, Takahiro Yamazaki, Hiromichi Ohta, Kyoko Shima, Katsuhide Ohi, Shigeru Nishiyama, Takeshi Sugai

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

Oxazolidinones were effectively prepared from N-carbamylamino alcohols by treatment with nitrous acid, via N-nitroso compound as the intermediate. A new route to (R)-4-benzyloxazolidinone was developed starting from DL- phenylalanine, utilizing D-hydantoinase-catalyzed enantioselective hydrolysis of 5-benzylhydantoin under the dynamic kinetic resolution conditions, and the subsequent reduction to the precursor for the above-mentioned cyclization reaction, by taking advantage of the intermediates bearing an N-carbamylamino functionality.

Original languageEnglish
Pages (from-to)189-192
Number of pages4
JournalSynlett
Issue number2
DOIs
Publication statusPublished - 2000 Jan 1

Keywords

  • Enzymes
  • Hydrolysis
  • N-carbamylamino alcohols
  • N-nitrosourea
  • Oxazolidinones

ASJC Scopus subject areas

  • Organic Chemistry

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