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Synthesis 1996; 1996(8): 954-958
DOI: 10.1055/s-1996-4328
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Lipase-Mediated Resolution of trans-1-Azidoindan-2-ol: A New Route to Optically Pure cis-1-Aminoindan-2-ol

Michiyasu Takahashi, Kunio Ogasawara*
  • *Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-77, Japan, Fax +81(22)2176845; E-mail c21799@cctu.cc.tohoku.ac.jp
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Publication Date:
31 December 2000 (online)

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Optically pure trans-1-azidoindan-2-ol has been prepared in both enantiomeric forms via lipase-mediated kinetic transesterification in organic solvent. A route to optically pure cis-1-aminoindan-2-ol has also been developed by using the optically pure trans-azidoalcohol thus obtained.

lipase-mediated resolution - (1S,2S)- and (1R,2R)-trans-azidoindan-2-ol - (1S,2R)- and (1R,2S)-cis-aminoindan-2-ol - Mitsunobu inversion - HIV protease inhibitor - chiral auxiliary