Tetrahedron Asymmetry p. 59 - 62 (2001)
Update date:2022-08-05
Topics: Lipase Enantiomeric excess (ee) Acetylation Nucleophilic addition Workup Reaction Monitoring Chiral HPLC Kinetic Resolution Racemic mixture Catalytic amount ritter reaction
Nakano, Shigeru
Igarashi, Yoshio
Nohira, Hiroyuki
Lipase-mediated kinetic resolution of cis-1,2-indandiol 5 in the presence of lipase PS was examined. Enantiomerically enriched (1S,2R)-2-acetoxy-1-indanol 6a was obtained when cis-1,2-indandiol 5 was treated with one equivalent of vinyl acetate. Treatment of 5 with two equivalents of vinyl acetate furnished a mixture of (1R,2S)-2-acetoxy-1-indanol 6a and (1R,2S)-1-acetoxy-2-indanol 6b. A route to both enantiomers of 1 was also developed by using the enantiomerically enriched mono-acetate thus obtained.
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Doi:10.1016/S0040-4039(02)00297-6
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