Table 7. SAR and SSR Studies of Hydrazone Ligands for the Coupling of 2-Methylnaphthylsilanolate (K+35a–).

| entry | ligand | time (h) | 37a (%) | 38b (%) | er, 37 (R/S)c |
|---|---|---|---|---|---|
| 1 | 13a | 2 | 81 | 2.0 | 6:94 |
| 2 | 13f | 2 | 86 | 1.4 | 5:95 |
| 3 | 21a | 4 | 70 | 3.5 | 40:60 |
| 4 | 21f | 6 | 76 | 2.8 | 43:57 |
| 5 | 29 | 4 | 78 | 6.6 | 48:52 |
| 6 | 15 | 2d | ∼21e | 12.8 | 50:50 |
| 7 | 33a | 2 | 84 | 3.0 | 19:81 |
| 8 | 33b | 18 | 59f | 9.0 | 68:32 |
| 9 | 34 | 24 | 34 | 8.8 | 52:48 |
Yield of chromatographed product taking into account of 1,1′-binaphthalene.
Percentage of 1,1′-binaphthalene in the chromatographed product estimated by CSP-SFC.
Ratio of (R)-37:(S)-37 determined by CSP-SFC.
Reaction stalled.
Contains a contaminant.
0.1 mmol scale.