Table 2. Optimization of the Temperature, Reaction Time, and Mole Fraction.
entry | catalyst (mol %) | time (h) | temp (°C) | yield (%)a | ee (%)b |
---|---|---|---|---|---|
1 | 5 | 24 | rt | 94 | 74 |
2 | 5 | 24 | 0 | 92 | 81 |
3 | 5 | 24 | –20 | 61 | 78 |
4 | 5 | 24 | –48 | 53 | 65 |
5 | 5 | 24 | –78 | 77 | 45 |
6 | 5 | 96 | 0 | 94 | 80 |
7 | 2.5 | 96 | 0 | 69 | 74 |
8 | 1 | 96 | 0 | 30 | 65 |
Isolated yield of S-benzyl thioester monocarboxylic acid.
The ee values were determined by chiral-phase HPLC using the OD-H column.