Tsuji–Wacker-Type Oxidation beyond Methyl Ketones: Reacting Unprotected Carbohydrate-Based Terminal Olefins through the “Uemura System” to Hemiketals and α,β-Unsaturated Diketones

A1 Journal article (refereed)


Internal Authors/Editors


Publication Details

List of Authors: Patrik A. Runeberg, Patrik C. Eklund
Publisher: American Chemical Society
Publication year: 2019
Journal: Organic Letters
Journal acronym: Org. Lett.
Volume number: 21
Issue number: 20
Start page: 8145
End page: 8148


Abstract

Aerobic Pd(AcO)2/pyridine-catalyzed oxidation of unprotected
carbohydrate-based terminal alkenes was studied. In accordance with
previous reports, the initial reaction step gave methyl ketones.
However, our substrates partially gave subsequent α,β-water elimination
and alcohol oxidation to α,β-unsaturated 2,5-diketones. Upon increasing
the pressure of O2, the reaction was shifted toward formation
of α,β-epoxy-2-ketones. The reactions were stereoselective and gave up
to quantitative conversions. However, isolated yields were substantially
lower because of the complexity of the product mixtures.


Last updated on 2020-26-02 at 06:04