The effect of molar ratio of β-keto ester 1a, oxime 2a and t-BuOOH on yields of the reaction products 3a and 4aa.
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|---|---|---|---|
| Entry | Molar ratio of 1a, 2a and t-BuOOH | Yield of 3ab (%) | Yield of 4ab (%) |
| 1 | 1 : 1 : 2 | 61 | Trace |
| 2 | 1 : 1 : 3 | 70 (64) | Trace |
| 3 | 1 : 1.5 : 2 | 81 (77) | n.d. |
| 4 | 1 : 2 : 2 | 76 | Trace |
| 5 | 1 : 3 : 2 | 60 | n.d. |
| 6 | 1 : 3 : 3 | 57 | Trace |
| 7 | 1.5 : 1 : 2 | 74 | 18 |
| 8 | 1.5 : 1 : 3 | 76 | 20 |
| 9 | 2 : 1 : 3 | 51 | 34 |
General reaction conditions: β-keto ester 1a (1–2 mmol), oxime 2a (1–3 mmol), Cu(BF4)2·6H2O (0.1 mmol, 10 mol%), t-BuOOH (70% aq.) (2–3 mmol), MeCN (5 mL) at 80 °C for 1 h.
Yields of 3a and 4a were determined based on 1H NMR using p-methoxyacetophenone as an internal standard; in the entries 2 and 3 isolated yields of 3a based on β-dicarbonyl compound are given in parenthesis. n.d. – not detected.