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

Tutkimustuotos: LehtiartikkeliArtikkeliTieteellinenvertaisarvioitu

4 Sitaatiot (Scopus)

Abstrakti

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.

AlkuperäiskieliEi tiedossa
Sivut8145–8148
JulkaisuOrganic Letters
Vuosikerta21
Numero20
DOI - pysyväislinkit
TilaJulkaistu - 2019
OKM-julkaisutyyppiA1 Julkaistu artikkeli, soviteltu

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