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On the mode of baker's yeast reduction of benzylidenecyclohexanone

Baker's yeast reduction of 1 in different experimental conditions, affords 3 or 5 and 7 in high yields and enantiomerically pure form. Baker's yeast reduction of benzylidene cyclohexanone 1 affords, as major transformation product, enantiomerically pure (S) carbinol 3, yielding in two step...

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Bibliographic Details
Published in:Tetrahedron letters 1995-01, Vol.36 (1), p.123-124
Main Authors: Fronza, Giovanni, Fogliato, Giovanni, Fuganti, Claudio, Lanati, Simonetta, Rallo, Roberta, Servi, Stefano
Format: Article
Language:English
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Summary:Baker's yeast reduction of 1 in different experimental conditions, affords 3 or 5 and 7 in high yields and enantiomerically pure form. 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/0040-4039(94)02190-M