Table 2. Selected results for genetic optimization of the artificial Suzukiase for the synthesis of 2-methoxy-1,1′-binaphthyl 8b.
Entry | Temp [°C] | Complex | Protein | ee [%] | TON |
1 | RT | 1 | — | rac | 20 |
2 | RT | 1 | WT | 58 (R) | 78 |
3 | RT | 1 | K121E | 76 (R) | 50 |
4 | RT | 1 | K121D | 34 (R) | 7 |
5 | RT | 1 | K121Q | 74 (R) | 20 |
6 | RT | 1 | K121M | 67 (R) | 59 |
7 | RT | 1 | K121F | 67 (R) | 38 |
8 | RT | 2 | K121A | 47 (S) | 32 |
9 | RT | 2 | S112M | 44 (S) | 53 |
10 | RT | 3 | S112M | 38 (R) | 78 |
11 | RT | 3 | S112A | 36 (R) | 52 |
12 | RT | 1 | S112M | 14 (S) | 58 |
13 | RT | 1 | S112A | 60 (R) | 58 |
14 | RT | 1 | N118K–K121E | 74 (R) | 73 |
15 | RT | 1 | N118S–K121E | 76 (R) | 79 |
16 | RT | 1 | N118E–K121E | 76 (R) | 75 |
17 | RT | 1 | N118L–K121E | 72 (R) | 86 |
18 | RT | 1 | S112W–K121E | 76 (R) | 64 |
19 | RT | 1 | S112N–K121E | 69 (R) | 61 |
20 | RT | 1 | S112A–K121E | 70 (R) | 80 |
21 | RT | 1 | S112Y–K121E | 80 (R) | 90 |
22 | RT | 1 | S112Y–K121E | 80 (R) | 160 a |
23 | 16 | 1 | S112Y–K121E | 84 (R) | 50 |
24 | 4 | 1 | S112Y–K121E | 86 (R) | 50 b |
25 | 4 | 1 | S112Y–K121E | 90 (R) | 50 c |
a0.50 mol% catalyst loading, 0.25 mol% Sav (tetramer) loading.
b0.50 mol% catalyst loading, 0.25 mol% Sav (tetramer) loading, after 7 days.
cPreparative scale (100 μmol). All reactions were performed in duplicate: Δee = ±1%, Δconv. = ±5%.