66841-45-0

Upstream product

• 40421-52-1 (1RS,2SR)-1-phenylpropane-1,2-diol 
• 98-88-4 benzoyl chloride 
• 873-66-5 1-propenylbenzene 
• 532-31-0 silver benzoate 
• 766-90-5 cis-1-phenyl-1-propylene 
• 40421-51-0 (1R,2R)-1-phenylpropane-1,2-diol 
• 100-52-7 benzaldehyde 
• 1798-60-3 (R)-1-hydroxy-1-phenyl-2-propanone 
• 40421-52-1 (1R,2S)-1-phenylpropane-1,2-diol 

Downstream Products

• 132538-08-0 (1R,2S)-(+)-1-cyclohexyl-1,2-propanediol 
• 88196-06-9 syn-1-phenylpropane-1,2-diol 
• 40421-52-1 (1R,2S)-1-phenylpropane-1,2-diol 

Relevant academic research and scientific papers

PREPARATION OF BOTH ENANTIOMERS OF (1R*, 2S*)-1-CYCLOHEXYL-1,2-PROPANEDIOL FROM THE COMMERCIAL NEUBERG'S KETOL

Both the optically pure enantiomers of (1R*,2S*)-1-cyclohexyl-1,2-propanediol (II) were prepared from commercial (R)-(-)-1-phenyl-1-hydroxy-2-propanone (I; Neuberg's ketol). (1R,2S)-(+)-1-Cyclohexyl-1,2-propanediol(+)-II) was obtained in 19percent total yield, its (1S,2R)-enantiomer ((-)II) in 8percent yield.Both diols, as well as their precursors, enantiomeric (1R*,2S*)-1-phenyl-1,2-propanediols (IIIa), are suitable chiral synthons.

Reductive C2-Homologation of Substituted Benzaldehydes by Fermenting Baker's Yeast

Reduction of benzaldehyde and substituted benzaldehydes with actively fermenting baker's yeast afforded optically active 1-arylpropane-1,2-diols in fairly good yields, as well as benzylic alcohols.It was revealed that benzaldehydes substituted with electron-withdrawing groups, which were previously reported to result only corresponding benzylic alcohols, were also reduced to give propanediol compounds in moderate yields.The reaction was shown to be highly diastereo-selective for erythro diols (>97percent d.e.).The optical purities of the erythro isomers (1R,2S) were also extremely high (>97percent e.e.), and single recrystallization of dibenzoates gave optically pure diol derivatives within the limits of HPLC analysis.