Traceless OH-Directed Wacker Oxidation-Elimination, an Alternative to Wittig Olefination/Aldol Condensation: One-Pot Synthesis of α,β-Unsaturated and Nonconjugated Ketones from Homoallyl Alcohols.
Department of Chemistry, Indian Institute of Technology Bombay , Powai, Mumbai, 400076 Maharashtra, India.
- Published Article
The Journal of Organic Chemistry
American Chemical Society
- Publication Date
Sep 16, 2016
A new method for one-pot synthesis of β-substituted and β,β-disubstituted α,β-unsaturated methyl ketones from homoallyl alcohols by sequential PdCl2/CrO3-promoted Wacker process followed by an acid-mediated dehydration reaction has been developed. Remarkably, internal homoallyl alcohols delivered regioselectively nonconjugated unsaturated carbonyl compounds under the same protocol. A new starting material-based synthesis of α,β-unsaturated and nonconjugated methyl ketones is demonstrated.
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The corresponding record at NLM can be accessed at https://www.ncbi.nlm.nih.gov/pubmed/27562136