Table 15.
Solvent-free asymmetric HDA reaction of aldehyde with Danishefsky's diene as illustrated in Eq 8.
| aldehydes | (L5)2Ti |
(L5)(L6)Ti |
||||||
|---|---|---|---|---|---|---|---|---|
| loading (%) | time (h) | yield (%) | ee (%) | loading (%) | time (h) | yield (%) | ee (%) | |
| benzaldehyde | 0.05 | 24 | >99 | 99.3 | 0.05 | 24 | 82 | 99.4 |
| p-anisaldehyde | 0.05 | 48 | >99 | 90.8 | 0.05 | 48 | >99 | 98.0 |
| m-anisaldehyde | 0.05 | 48 | 81 | 96.6 | 0.05 | 48 | 82.6 | 99.8 |
| o-anisaldehyde | 0.05 | 48 | 95 | 75.1 | 0.05 | 48 | >99 | 95.1 |
| 3-phenylpropionaldehyde | 0.05 | 96 | >99 | 97.9 | 0.05 | 96 | >99 | 98.3 |
| trans-cinnamaldehyde | 0.1 | 96 | 82 | 98.4 | 0.05 | 96 | 56.6 | 96.6 |
| furfural | 0.05 | 48 | >99 | 99.2 | 0.05 | 48 | >99 | 99.7 |
| furfural | 0.01 | 96 | 37 | 94.7 | 0.01 | 96 | >99 | 97.7 |
| furfural | - | - | - | - | 0.005 | 144 | 63 | 96.2 |
| m-tolualdehyde | 0.1 | 48 | 95 | 98.5 | 0.05 | 48 | 92 | 99.5 |
| 1-naphthaldehyde | 0.05 | 48 | 55 | 85.6 | 0.05 | 48 | 65 | 98.5 |
| p-cyanobenzaldehyde | 0.1 | 48 | >99 | 92.9 | 0.05 | 48 | 98.4 | 97.9 |
| m-bromobenzaldehyde | 0.1 | 48 | >99 | 97.4 | 0.05 | 48 | 98.3 | 97.6 |
| p-bromobenzaldehyde | 0.05 | 48 | >99 | 98.0 | 0.05 | 48 | >99 | 98.4 |
| p-chlorobenzaldehyde | 0.05 | 48 | >99 | 91.2 | 0.05 | 48 | >99 | 99.1 |
| p-nitrobenzaldehyde | 0.05 | 48 | >99 | 97.3 | 0.05 | 24 | >99 | 99.4 |