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

Venkati Bethi and Rodney A. Fernandes*

*Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076 Maharashtra, India, Email: rfernandchem.iitb.ac.in

V. Bethi, R. A. Fernandes, J. Org. Chem., 2016, 81, 8577-8584.

DOI: 10.1021/acs.joc.6b01899

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Abstract

A sequential PdCl₂/CrO₃-promoted Wacker process followed by an acid-mediated dehydration enables the synthesis of β-substituted and β,β-disubstituted α,β-unsaturated methyl ketones from homoallyl alcohols with a terminal double bond, whereas internal homoallyl alcohols delivered regioselectively nonconjugated unsaturated carbonyl compounds under the same protocol.

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Key Words

Wacker-Tsuji Oxidation, Chromium Trioxide, oxidation, elimination

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ID: J42-Y2016