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Optimization of the Intramolecular C—H Oxidation
 | |||||
|---|---|---|---|---|---|
| entry | additive | quinone | Pd catalyst | isolated yield | dr (anti:syn)a |
| 1 | none | BQ | 1 | 38 | 9:1 |
| 2 | DIPEA | BQ | 1 | 46 | 7:1 |
| 3 | Cr(salen)Cl | BQ | 1 | 83 | 9:1 |
| 4 | none | 2,6-Me2BQ | 1 | 0 | nd |
| 5 | none | BQ | Pd(OAc)2 | >5 | nd |
| 6 | Cr(salen)Cl | BQ | none | 0 | nd |
Diastereomeric ratio determined by 1H NMR of the crude reaction after workup. DIPEA = diisopropylethylamine.
