Syntheses of trans-(1R,2R) and cis-(1S,2R)-1-amino-2-indanol (Al) were accomplished by a series of enantioselective enzymatic reactions using lipase and transaminase (TA). Lipase catalysed enantioselective hydrolysis of 2-acetoxyindanone was employed to prepare (R)-2-hydroxy inclanone (HI). trans-Al (5 mM) (de > 98%) was produced from 20 mM (R)-2- HI using omega-TA and 50 mM (S)-1-aminoindan as an amino donor in water-saturated ethyl acetate. For the production of cis-Al, the diastereomeric (2R)-Al was synthesized from (R)-2-HI using reductive amination, and the kinetic resolution was performed with omega-TA. The enantioselectivity of co-TA for (2R)-Al was increased to 22.1 in the presence of 5% gamma-cyclodextrin. cis-Al (15.4 mM) (96% de) was obtained from 40 mM (2R)-Al using 30 mM pyruvate and omega-TA (25 mg) in 10 mL of 100 mM phosphate buffer (pH 7.0). (c) 2005 Wiley Periodicals, Inc.