Table 2. Catalytic TH of Carbonyl Compounds (0.1 M) to Alcohols with Complexes 8, 10, and 21 (S/C = 2000–10000) and NaOiPr (2 mol %) in 2-Propanol at 82 °C.
| entry | substrate | complex | S/C | time | conversiona (%) | TOFb (h–1) |
|---|---|---|---|---|---|---|
| 1 | b | 8 | 5000 | 20 h | 96 | 700 |
| 2 | b | 10 | 5000 | 18 h | 98 | 1800 |
| 3 | b | 21 | 5000 | 18 h | 99 | 2500 |
| 4 | c | 8 | 10000 | 20 h | 86 | 1800 |
| 5 | c | 10 | 10000 | 18 h | 78 | 19000 |
| 6 | c | 21 | 10000 | 2 h | 85 | 59000 |
| 7 | d | 8 | 5000 | 1.5 h | 98 | 19000 |
| 8 | d | 10 | 5000 | 10 min | 98 | 30000 |
| 9 | d | 21 | 5000 | 5 min | 99 | 150000 |
| 10 | e | 8 | 2000 | 20 h | 86c | 1100 |
| 11 | e | 10 | 2000 | 18 h | 98d | 7000 |
Conversions have been determined by GC analyses.
Turnover frequency (moles of ketone converted to alcohol per mole of catalyst per hour) at 50% conversion.
Mixture of diastereoisomeric alcohols: (+)-neomenthol (58%), (+)-isomenthol (11%), (−)-menthol (15%), (+)-neoisomenthol (16%).
Mixture of diastereoisomeric alcohols: (+)-neomenthol (65%), (+)-isomenthol (11%), (−)-menthol (15%), (+)-neoisomenthol (9%).