TY - JOUR
T1 - Synthesis of enantiomers of indanoxazolidinone based on the lipase-catalyzed resolution of the corresponding N-carbamylamino derivative
AU - Suzuki, Masumi
AU - Nagasawa, Chiaki
AU - Sugai, Takeshi
N1 - Funding Information:
The authors thank Amano Enzyme Co., Roche Diagnostics Co. and Toyo Denka Kogyo, for the generous gifts of lipase PS, Chirazyme ® L-2 and Toyonite 200-M, respectively. We are grateful to Professor Shigeru Ohba of Keio University for X-ray analysis. We also express our thanks to Dr Harumi Kaga of Hokkaido National Industrial Research Institute and Professor Tadashi Kometani of Toyama National College of Technology for their discussion. This work was accomplished as ‘Science and Technology Program on Molecules, Supra-Molecules and Supra-Structured Materials’ of an Academic Frontier Promotional Project, by Japan's Ministry of Education, Culture, Sports, Science and Technology, and acknowledged with thanks. This work was also supported by a Grant-in-Aid for Scientific Research (No. 12660120).
PY - 2001/6/4
Y1 - 2001/6/4
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
KW - Oxazolidinones
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U2 - 10.1016/S0040-4020(01)00454-9
DO - 10.1016/S0040-4020(01)00454-9
M3 - Article
AN - SCOPUS:0035806158
SN - 0040-4020
VL - 57
SP - 4841
EP - 4848
JO - Tetrahedron
JF - Tetrahedron
IS - 23
ER -