On the Mode of Baker's Yeast Reduction of Benzylidenecyclohexanone

Article abstract of DOI:10.1016/0040-4039(94)02190-M

Baker's yeast reduction of benzylidene cyclohexanone 1 affords, as major transformation product, enantiomerically pure (S) carbinol 3, yielding in two steps (2S) 2-acetoxycyclohexanone 6, close to nearly racemic saturated ketone 4, whereas carbinol 5 and its enantiomer 8 can be obtained from 3 upon LiAlH4 reduction upon baker's yeast reduction to 7, followed by inversion of configuration, respectively. - Keywords: baker's yeast, reduction, enantioselectivity, diastereoselectivity