L. Nunno, C. Franchini, A. Scilimati
Apr 1, 2000
Citations
0
Influential Citations
26
Citations
Journal
Tetrahedron-asymmetry
Abstract
Abstract Several methods have been developed to prepare 1-(benzothiazol-2-ylsulfanyl)-3-chloropropan-2-ol 2 with good to high enantiomeric excess: 70 and 93% ees have in fact been obtained by baker's yeast-induced asymmetric reduction of the ketone precursor 1 and by kinetic resolution performed in the presence of lipase from Pseudomonas sp. (E=38), respectively. Compounds (R)-(+)-2 and (S)-(−)-2 have also been prepared by a chemical method in 90% yield and with enantiomeric excesses of 98 and 96.4%, respectively. HPLC on Chiralcel OD column separation of enantiomers (separability factor α=1.64) has also been successfully performed. Compound 2 could, in turn, be used for the synthesis in an optically active form of various molecules, including β-aminoalcohols 6, drugs with potential β-blocker activity.