Entrya | Ketone | Catalyst | Time (h) | Conversion [%]b | e.e. [%]c |
|---|
1 |
9a
| (R,R)-8 (0.5%) | 16 | >99 | 3 |
2 |
10a
| (R,R)-8 (0.5%) | 16 | >99 | 80 (S) |
3 |
10a
| (R,R)-3 (0.5%) | 16 | >99 | 74 (S) |
4 |
10a
| (R,R)-8 (0.33%) | 1 | 44 | 56 (S) |
5 |
10a
| (S,S)-3 (0.33%) | 1 | 45 | 65 (R) |
6 |
11a
| (R,R)-8 | 16 | >99 | 9 |
7 |
12a
| (R,R)-8 | 16 | >99 | 98d |
8 e |
12a
| (R,R)-3 | 16 | >99 | 98f |
- aReactions were carried out using 0.33 mmol mL-1 of ketone, 0.5 mol% preformed catalyst (R,R)-27 and 1 mol% KOtBu at 70°C and 50 bar of hydrogen pressure with a 16 h reaction time. bConversions were determined by 1H NMR analysis of the crude reaction mixtures (all peaks assigned). cThe e.e. value was determined by chiral HPLC (Chiralpak AD-H/Chiralcel OD-H column). The absolute configuration was determined to be S by comparison of optical rotation values with literature values. d ((R,R) + (S,S)):meso 3.1:1. e Reaction temperature of 50°C. f {(R,R) + (S,S)}:meso 2.8:1.
