Baker's yeast-induced asymmetric reduction of α-ketosulfides: synthesis of optically active 1-(benzothiazol-2-ylsulfanyl)-2-alkanols, 2-alkanols, and thiiranes

L Di Nunno, C Franchini, A Nacci, A Scilimati…

Index: Di Nunno, Leonardo; Franchini, Carlo; Nacci, Angelo; Scilimati, Antonio; Sinicropi, Maria Stefania Tetrahedron Asymmetry, 1999 , vol. 10, # 10 p. 1913 - 1926

Full Text: HTML

Citation Number: 26

Abstract

1-(Benzothiazol-2-ylsulfanyl)-2-alkanols 3 were prepared in very high enantiomeric excess by baker's yeast-induced asymmetric reduction of 1-(benzothiazol-2-ylsulfanyl)-2-alkanones 1. Conversion of 3 into optically active simple 2-alkanols 4 and thiiranes 2 by reductive desulfurization and base treatment, respectively, is also described. The absolute configuration of the new compounds synthesized has been established by chemical ...