Synthesis of Optically Active 1,2-Indene Oxide and Vicinal cis-Aminoindanols via Asymmetric Reduction of 2-Tolylsulfonyloxy-1-indanone with (-)-B-Chlorodiisopinocampheylborane

and Ok Kyoung ChoiDepartment of Chemistry, Hallym University, Chunchon, Kangwondo 200-702, KoreaReceived July 18, 2001Keywords : (−)-B-Chlorodiisopinocampheylborane, (1S,2R)-1,2-Indene oxide, (1S,2R)-1-Amino-2-indanol,(1S,2R)-2-Amino-1-indanol, Asymmetric reduction.Optically active vicinal cis-aminoindanols such as (1S,2R)-1-amino-2-indanol 1 and (1S,2R)-2-amino-1-indanol 2 areimportant substances which can be widely used as a vitalsource of an orally active HIV-1 protease inhibitor, Indinavir,and as chiral ligands or auxiliaries for chiral stationary phaseand asymmetric transformations including carbonyl reductions,aldol reactions, diethylzinc addition to aldehydes and Diels-Alder reactions.