Elongation of β-hydroxyenones by cross-metathesis |
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Authors: | Franck A Silva |
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Institution: | Chemistry Research Laboratory, 12 Mansfied Road, University of Oxford, OX1 3TA, UK |
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Abstract: | Enantioenriched aldol products derived from enones are notoriously difficult to prepare due to their sensitivity to retro-aldolisation, elimination and the requirement of a large excess of the enone donor for their preparation. However, some success has been obtained for the preparation of aldol products derived from methylvinylketone and pentenone using zinc-dinuclear catalysts or catalytic antibodies. Herein, we describe how simple first-generation hydroxyenones can be easily elongated by alkene exchange with structurally diverse olefinic partners in the presence of Ru-based metathesis catalysts allowing for the preparation of aldol products difficult to access by direct aldolisation. The data suggest that even though unprotected aldols are suitable for these cross-metathesis reactions, silyl-protected β-hydroxyenones generally afforded the desired elongated products in much higher chemical yields. |
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Keywords: | Cross-metathesis Hydroxyenones Aldol reaction |
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