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.
Original language | Undefined/Unknown |
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Pages (from-to) | 8145–8148 |
Journal | Organic Letters |
Volume | 21 |
Issue number | 20 |
DOIs | |
Publication status | Published - 2019 |
MoE publication type | A1 Journal article-refereed |