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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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Published in: | Tetrahedron letters 1995-01, Vol.36 (1), p.123-124 |
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Main Authors: | , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/0040-4039(94)02190-M |