Synthesis of enantiomers of indanoxazolidinone based on the lipase-catalyzed resolution of the corresponding N-carbamylamino derivative

Masumi Suzuki, Chiaki Nagasawa, Takeshi Sugai

研究成果: Article査読

14 被引用数 (Scopus)

抄録

Enantiomerically enriched (4R,5S)- and (4S,5R)-indano[1,2-d]oxazolidinones were enzymatically prepared from (±)-1-amino-2-indanol. Racemic 1-(N′-chloroacetyl-N-carbamylamino)-2-indanol O-chloroacetate was hydrolyzed with immobilized Pseudomonas cepacia lipase in the presence of β-cyclodextrin in acetone-buffer solution, to afford (1S,2R)-1-(N′-chloroacetyl-N-carbamylamino)-2-indanol (90%e.e.) and the unreacted (1R,2S)-substrate (97%e.e.), in nearly quantitative yields. The deprotection provided enantiomers of 1-N-carbamylamino-2-indanol, the precursor of indanoxazolidinone, via nitrosation-deaminocyclization reaction.

本文言語English
ページ(範囲)4841-4848
ページ数8
ジャーナルTetrahedron
57
23
DOI
出版ステータスPublished - 2001 6月 4

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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