Organic Chemistry Portal

Abstracts

Search:

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 (free Supporting Information)


see article for more reactions

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.

see article for more examples



Key Words

Wacker-Tsuji Oxidation, Chromium Trioxide, oxidation, elimination


ID: J42-Y2016