Traceless OH-Directed
Wacker Oxidation-Elimination,
an Alternative to Wittig Olefination/Aldol Condensation: One-Pot Synthesis
of <i>α</i>,<i>β</i>‑Unsaturated
and Nonconjugated Ketones from Homoallyl Alcohols
Venkati Bethi
Rodney A. Fernandes
10.1021/acs.joc.6b01899.s001
https://acs.figshare.com/articles/journal_contribution/Traceless_OH-Directed_Wacker_Oxidation-Elimination_an_Alternative_to_Wittig_Olefination_Aldol_Condensation_One-Pot_Synthesis_of_i_i_i_i_Unsaturated_and_Nonconjugated_Ketones_from_Homoallyl_Alcohols/3811392
A new method for
one-pot synthesis of <i>β-</i>substituted and <i>β</i>,<i>β</i><b>-</b>disubstituted <i>α</i>,<i>β</i>-unsaturated methyl ketones
from homoallyl alcohols by sequential
PdCl<sub>2</sub>/CrO<sub>3</sub>-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 <i>α</i>,<i>β</i>-unsaturated and nonconjugated methyl ketones is demonstrated.
2016-08-26 00:00:00
Olefination
compound
acid-mediated dehydration reaction
sequential
homoallyl alcohols
Wittig
Homoallyl
β-
method
Synthesi
Condensation
Ketone
PdCl
Traceless OH-Directed Wacker Oxidation-Elimination
one-pot
Nonconjugated
nonconjugated methyl ketones
Remarkably
carbonyl
disubstituted
CrO
material-based
One-Pot
Alternative
synthesis
Unsaturated
regioselectively