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Baker's yeast reduction of (E)-1-phenyl-1,2-propanedione 2-(O-methyloxime). A key step for a (−)-norephedrine synthesis

1997; Elsevier BV; Volume: 8; Issue: 15 Linguagem: Inglês

10.1016/s0957-4166(97)00280-2

1362-511X

Olyr C. Kreutz, Paulo J. S. Moran, J. Augusto R. Rodrigues,

Chemical synthesis and alkaloids

The enantioselective Baker's yeast reduction of (E)-1-phenyl-1,2-propanedione 2-(O-methyloxime) 1 afforded (−)-(R)-1-hydroxy-1-phenyl-2-propanone 2-(O-methyloxime) 2 with 97% of enantiomeric excess (ee) which was diastereoselectively reduced by LiAlH4 to obtain the (−)-(R,S)-norephedrine with ee=82% and (−)-(R,R)-norpseudoephedrine with ee=93% in a ratio 4:1 respectively.