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
Publication statusPublished - 2000

Fingerprint

dihydropyrimidinase
Bearings (structural)
Nitrous Acid
Nitroso Compounds
Oxazolidinones
Cyclization
Phenylalanine
Hydrolysis
Alcohols
Kinetics
Nitrosation
5-benzylhydantoin

Keywords

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

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Suzuki, M., Yamazaki, T., Ohta, H., Shima, K., Ohi, K., Nishiyama, S., & Sugai, T. (2000). N-carbamylamino alcohols as the precursors of oxazolidinones via nitrosation-deamination reaction. Synlett, (2), 189-192.

N-carbamylamino alcohols as the precursors of oxazolidinones via nitrosation-deamination reaction. / Suzuki, Masumi; Yamazaki, Takahiro; Ohta, Hiromichi; Shima, Kyoko; Ohi, Katsuhide; Nishiyama, Shigeru; Sugai, Takeshi.

In: Synlett, No. 2, 2000, p. 189-192.

Research output: Contribution to journalArticle

Suzuki, M, Yamazaki, T, Ohta, H, Shima, K, Ohi, K, Nishiyama, S & Sugai, T 2000, 'N-carbamylamino alcohols as the precursors of oxazolidinones via nitrosation-deamination reaction', Synlett, no. 2, pp. 189-192.
Suzuki M, Yamazaki T, Ohta H, Shima K, Ohi K, Nishiyama S et al. N-carbamylamino alcohols as the precursors of oxazolidinones via nitrosation-deamination reaction. Synlett. 2000;(2):189-192.
Suzuki, Masumi ; Yamazaki, Takahiro ; Ohta, Hiromichi ; Shima, Kyoko ; Ohi, Katsuhide ; Nishiyama, Shigeru ; Sugai, Takeshi. / N-carbamylamino alcohols as the precursors of oxazolidinones via nitrosation-deamination reaction. In: Synlett. 2000 ; No. 2. pp. 189-192.
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AU - Ohi, Katsuhide

AU - Nishiyama, Shigeru

AU - Sugai, Takeshi

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