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. Author manuscript; available in PMC: 2018 Nov 22.
Published in final edited form as: Org Biomol Chem. 2017 Nov 22;15(45):9570–9574. doi: 10.1039/c7ob02283b

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%)
a

Yields were estimated by 1H NMR analysis of the crude reaction mixture.

b

One equivalent of XtalFluor-E® was used

c

XtalFluor-M® (10 mol%) was used instead of XtalFluor-E®.

d

MeOH:DCM (1:1 v:v, 0.1 M) was used.