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

Masumi Suzuki, Chiaki Nagasawa, Takeshi Sugai

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)4841-4848
Number of pages8
JournalTetrahedron
Volume57
Issue number23
DOIs
Publication statusPublished - 2001 Jun 4

Fingerprint

Enantiomers
Lipase
Derivatives
Nitrosation
Oxazolidinones
Burkholderia cepacia
Cyclodextrins
Acetone
Buffers
Substrates
2-indanol

Keywords

  • Enzymes and enzyme reactions
  • Hydrolysis
  • Nitroso compounds
  • Oxazolidinones

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of enantiomers of indanoxazolidinone based on the lipase-catalyzed resolution of the corresponding N-carbamylamino derivative. / Suzuki, Masumi; Nagasawa, Chiaki; Sugai, Takeshi.

In: Tetrahedron, Vol. 57, No. 23, 04.06.2001, p. 4841-4848.

Research output: Contribution to journalArticle

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AU - Suzuki, Masumi

AU - Nagasawa, Chiaki

AU - Sugai, Takeshi

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N2 - 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.

AB - 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.

KW - Enzymes and enzyme reactions

KW - Hydrolysis

KW - Nitroso compounds

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