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

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Publikationens författare: Patrik A. Runeberg, Patrik C. Eklund
Förläggare: American Chemical Society
Publiceringsår: 2019
Tidskrift: Organic Letters
Tidskriftsakronym: Org. Lett.
Volym: 21
Nummer: 20
Artikelns första sida, sidnummer: 8145
Artikelns sista sida, sidnummer: 8148


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.

Senast uppdaterad 2020-07-07 vid 04:35