Enantioselective Synthesis of (S)-2-Methyl-1-alkanols via Bakers'Yeast Mediated Reduction of α-Methyl-2-thiophenepropenals

Article abstract of DOI:10.1021/jo00033a028

The bakers'yeast mediated enantioselective reductions of some α-methyl-5-(1-alkyl)-2-thiophenepropenals 3 are described.These furnished (S)-β-methyl-5-(1-alkyl)-2-thiophenepropanols 5 in good to high enantiomeric excesses (76-98percent ee).An alternative approach to (S)-β-methyl-5-(1-alkyl)-2-thiophenepropanols 5d-f (98percent ee) is also described.Raney nickel reduction of their acetates, followed by hydrolysis, provided (S)-2-methyl-1-alkanols 2b-f of unchanged optical purities.