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Key optimizations of allylation chemistry using d-threoninol as the model substrate
| ||||||
|---|---|---|---|---|---|---|
| entry | catalyst chirality | catalyst loading (mol eq.) | time (days) | temperature °C) | percent conversiona | product ratio 8:17 |
| 1 | (R) | 0.05 | 2 | 100 | trace | 1:0 |
| 2 | (R) | 0.1 | 2 | 100 | 27% | 1:0 |
| 3 | (R) | 0.1 | 7 | 100 | 41% | 1:0 |
| 4 | (S) | 0.1 | 7 | 100 | 27% | 0:1 |
| 5 | (R) | 0.2 | 4 | 100 | 51% | 1:0 |
| 6 | (S) | 0.2 | 4 | 100 | 37% | 0:1 |
| 7 | (R) | 0.2 | 4 | 110 | 58% | 1:0 |
> 20:1 diastereomeric ratio determined.
