Development of the scope of a co-mediated O-->C rearrangement reaction |
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Authors: | Meek Simon J Pradaux Fabienne Carbery David R Demont Emmanuel H Harrity Joseph P A |
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Affiliation: | Department of Chemistry, University of Sheffield, Brook Hill, Sheffield, S3 7HF, UK. |
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Abstract: | reaction: see text] In this paper we describe an Al-promoted, Co-mediated O-->C rearrangement reaction of cyclic enol ethers. This process delivers functionalized cyclohexanones with good to excellent levels of diastereocontrol, whereby the product stereochemistry is dependent on the E/Z-stereochemistry of the starting enol ether. The rearrangement process also permits access to highly substituted alpha-spirocyclic cyclohexanones as well as cyclopentanones. The latter rearrangement appears to proceed via an unusual 5-(enolendo)-exo-trig cyclization process. |
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