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

doi:10.1055/s-2000-6508

Synlett 2000; 2000(2): 189-192
DOI: 10.1055/s-2000-6508

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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

^*Department of Chemistry, Keio University, 3-14-1 Hiyoshi, Yokohama 223-8522, Japan; Fax +81 45 5 63 59 67; E-mail: sugai@chem.keio.ac.jp

Abstract

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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.

N-carbamylamino alcohols - N-nitrosourea - enzymes - hydrolysis - oxazolidinones

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