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Stereoselective spirodiepoxide formation: Influence of allene structure.
| selectivitya | ||||||
|---|---|---|---|---|---|---|
| entry | allene | R1 | R2 | product | r1 | r2 |
| 1 | 1 | i-Bu | CH2OTBS | 10 | >20:1 | 2:1 |
| 2 | 6 | i-Pr | i-Pr | 11 | >20:1 | 3.3:1 |
| 3 | 7a | i-Bu |
|
12a | >20:1 | 5:1 |
| 4 | 7b | i-Bu |
|
12b | >20:1 | 1:1 |
| 5 | 8 | i-Bu |
|
13 | >20:1 | 6:1 |
| 6 | 9 | CH2OTBS |
|
14 | >20:1 | 8:1 |
