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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.

Authors
  • Bethi, Venkati1
  • Fernandes, Rodney A1
  • 1 Department of Chemistry, Indian Institute of Technology Bombay , Powai, Mumbai, 400076 Maharashtra, India. , (India)
Type
Published Article
Journal
The Journal of Organic Chemistry
Publisher
American Chemical Society
Publication Date
Sep 16, 2016
Volume
81
Issue
18
Pages
8577–8584
Identifiers
DOI: 10.1021/acs.joc.6b01899
PMID: 27562136
Source
Medline
License
Unknown

Abstract

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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