Table 1.
Optimization results for the XtalFluor-E® mediated N,O-acetal formation of enamide
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| Entry | Solvent | Time (h) | Conversion (yield)a |
| 1b | MeOH | 36 | 99% (>98%) |
| 2 | MeOH | 48 | 88% (57%) |
| 3 | Toluene | 22 | 74% (66%) |
| 4 | CH2Cl2 | 10 | 95% (89%) |
| 5 | CHCl3 | 10 | 93% (83%) |
| 6 | Nitromethane | 10 | 95% (85%) |
| 7 | ClCH2CH2Cl | 10 | 95% (85%) |
| 8 | Acetonitrile | 22 | 85% (68%) |
| 9c | CH2Cl2 | 36 | 97% (86%) |
| 10d | CH2Cl2 | 8 | 100% (>98%) |
Yields were estimated by 1H NMR analysis of the crude reaction mixture.
One equivalent of XtalFluor-E® was used
XtalFluor-M® (10 mol%) was used instead of XtalFluor-E®.
MeOH:DCM (1:1 v:v, 0.1 M) was used.