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| entry | solvent | ratio 12a:13a | yield 13a |
|---|---|---|---|
| 1 | hexanes | 1.0:0 | 0% |
| 2 | toluene | 1.0:0 | 0% |
| 3 | Et2O | 1.0:0 | 0% |
| 4 | THF | 2.2:1.0 | 48% |
| 5 | THF + 18-C-6 | 1.7:1.0 | 50% |
| 6 | DME | 1.2:1.0 | 64% |
| 7 | diglyme | 1.1:1.0 | 91% |
Conditions: Deprotonation of cyclopentanecarboniirile (2.0 equiv) with LDA (2.1 equiv) at −78 °C followed by addition of 10a (1.0 equiv). After 1 h at-78 °C, added electrophile (2.1 equiv).
