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. 2018 Feb 5;8(11):5670–5677. doi: 10.1039/c7ra13587d

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
a

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.

b

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.