Table 4.
Entry | pH | Conv. (1.5 h)[b] [%] |
Yield (1.5 h)[b] [%] |
ee (1.5 h)[c] [%] |
ee (24 h)[c] [%] |
---|---|---|---|---|---|
1 | 5.0 | 2 | 1 | >99 | 93 |
2 | 5.5 | 5 | 3 | >99 | 93 |
3 | 6.0 | 13 | 12 | >99 | 91 |
4 | 6.5 | 24 | 22 | >99 | 87 |
5 | 7.0 | 27 | 26 | 99 | 79 |
6 | 7.5 | 28 | 27 | 98 | 62 |
7 | 8.0 | 33 | 31 | 97 | 41 |
8 | 8.5 | 32 | 31 | 95 | 13 |
9 | 9.0 | 31 | 30 | 92 | 0 |
Conditions: The reactions contained Bis-Tris/HEPPS/CHES buffer (75 mM/38 mM/38 mM, respectively, 1 mL total volume), alkene 3a (5 mM), PETNR (0.02 μM), and NADPH (6 mM). Reactions were agitated at 30 °C at 130 rpm for 1.5 and 24 h. Alkene 3a was added as a DMF solution (2% final DMF concentration).
By GC using a DB-Wax column.
By GC using Chirasil-DEX-CB column.