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

Enantiomerically enriched (4R,5S)- and (4S,5R)-indano[1,2-d]oxazolidinones were enzymatically prepared from (+/-)-1-amino-2-indanol. Racemic 1-(N'-chl oroacetyl-N-carbamylamino)-2-indanol O-chloroacetate was hydrolyzed with im mobilized Pseudomonas cepacia Lipase in the presence of beta -cyclodextrin in acetone-buffer solution, to afford (1S,2R)-1-(N'-chloroacetyl-N-carbamyl amino)-2-indanol (90%e.e.) and the unreacted (1R,2S)-substrate (97%e.e.), i n nearly quantitative yields. The deprotection provided enantiomers of 1-N- carbamylamino-2-indanol, the precursor of indanoxazolidinone, via nitrosati on-deaminocyclization reaction. (C) 2001 Elsevier Science Ltd. All rights r eserved.