Table 2.
Entry | Reactant | Product | Time (h), yield |
---|---|---|---|
1 | 2: 2 h, 72% | ||
2 | 3: 6 h, 69% | ||
3 | 4a, 4b: 3 h, 48% 1:1 mixture | ||
4 | 5: 1 h, 50%[b] | ||
5 | NA[c] | – | |
6 | NA[c] | – [d] | |
7 | 6: 2 h, 84% |
Reactions were conducted at a 0.125 m concentration of 2-(trimethylsilyl)phenyl triflate in MeCN, in the presence of 1.2 equiv. of the enol ether (or vinylene carbonate), 2 equiv. of CsF, and 2 equiv. of 18-Cr-6 at room temperature.
Yield obtained with 3 equiv. of ethyl vinyl ether.
n.a.: not applicable.
About 86% of the glycal was recovered.