Table 3.
Entry | Carboxylate | Grignard reagent | Allene | Yield [%] |
---|---|---|---|---|
1 | 93 | |||
2 | 68 | |||
3 | 64 | |||
4 | 75 | |||
5 | 78 | |||
6 | CyMgCl | 71 | ||
7 | 63 | |||
8 | 90 | |||
9 | 70 | |||
10 | 61 | |||
11 | 61 | |||
12 | 31[b] (24)[c] 44[b] (34)[c] | |||
13 | 39 | |||
14 | 25(Bz) 24(Piv) 14(Ac) |
[a] Yield of product isolated from the reaction run with a 0.2 m solution of propargyl carboxylate (1–2 mmol) in Et2O, with dropwise addition of the Grignard reagent during 5 min. [b] From 0.25 mmol of substrate (R=Piv). [c] From 0.5 mmol of substrate (R=Ac).