Tetrahedron Letters p. 123 - 124 (1995)
Update date:2022-08-05
Topics:
Fronza, Giovanni
Fogliato, Giovanni
Fuganti, Claudio
Lanati, Simonetta
Rallo, Roberta
Servi, Stefano
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
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