Table 1. Probing the importance of boron positioning and substitution on oxime condensations.
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Entry | Ar | X | Product | Conc (µM) | Conv b (%) |
1 c | Ph | H | 100 | <5 | |
2 | H | 100 | >98 | ||
3 | H | 10 | >98 | ||
4 | H | 100 | >98 | ||
5 c | H | 100 | <5 | ||
6 c | H | 100 | <5 | ||
7 | Me | 100 | 94 | ||
8 | H | 100 | >98 d | ||
9 | Me | 100 | >98 |
aTime is approximate since samples are injected directly after mixing.
bDetermined by reverse phase HPLC analysis under neutral conditions.
cInjections at 90 minutes still show <5% conversion.
dAt the first injection approximately 10% of the pinacol ester oxime is observed, but only the hydrolysed product is detected at 90 minutes. KPi = potassium phosphate buffer.