Treatment of cyclic tert-trihalomethylcarbinols with CrCl(2) in THF/HMPA in the presence of aryl or aliphatic aldehydes initiates a cascade sequence of one carbon ring expansion-olefination affording conjugated exocyclic ketones. Acyclic tert-trihalomethylcarbinols undergo a comparable cascade of one carbon homologation-olefination.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2517229 | PMC |
| http://dx.doi.org/10.1021/ol061953q | DOI Listing |
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Ring expansion/homologation--aldehyde condensation cascade using tert-trihalomethylcarbinols.
Org Lett
September 2006
Department of Biochemistry, University of Texas Southwestern Medical Center, Dallas, Texas 75390, USA.
Treatment of cyclic tert-trihalomethylcarbinols with CrCl(2) in THF/HMPA in the presence of aryl or aliphatic aldehydes initiates a cascade sequence of one carbon ring expansion-olefination affording conjugated exocyclic ketones. Acyclic tert-trihalomethylcarbinols undergo a comparable cascade of one carbon homologation-olefination.
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