Table 2. Evaluation of the Ring-Closing Metathesis toward Goniothalamin (1) under Flow Conditions.
entry | R | conc. (M) | catalyst | loading (mol %) | T (°C) | t (min) | conv. (%)a | 1/17/19 or 1/18/20a | yield (1 + 19 or 1 + 20) (%)b |
---|---|---|---|---|---|---|---|---|---|
1 | H | 0.05 | Grubbs I | 10 | 100 | 16.0 | 23 | 100:0:0 | NDc |
2 | H | 0.01 | Grubbs II | 5 | 100 | 16.0 | 90 | 79:0:21 | 90 |
3 | H | 0.05 | Grubbs II | 5 | 50 | 16.0 | 100 | 38:44:18 | 55 |
4 | H | 0.05 | Grubbs II | 5 | 100 | 16.0 | 100 | 57:0:43 | 78 |
5 | H | 0.05 | Grubbs II | 1 | 100 | 16.0 | 55 | 83:0:17 | NDc |
6 | H | 0.05 | Grubbs II | 5 | 100 | 8.0 | 97 | 54:0:46 | 79 |
7 | H | 0.01 | Hoveyda II | 5 | 100 | 16.0 | 100 | 44:0:56 | 97 |
8 | H | 0.05 | Hoveyda II | 5 | 100 | 16.0 | 100 | 41:0:59 | 58 |
9 | Me | 0.05 | Grubbs I | 10 | 100 | 16.0 | 0 | ||
10 | Me | 0.01 | Grubbs II | 5 | 100 | 16.0 | 80 | 100:0:0 | 75 (1 only) |
11 | Me | 0.01 | Grubbs II | 5 | 100 | 32.0 | 75 | 100:0:0 | 65 (1 only) |
12 | Me | 0.05 | Grubbs II | 5 | 100 | 16.0 | 100 | 66:0:34 | 94 |
13 | Me | 0.01 | Hoveyda II | 5 | 100 | 16.0 | 100 | 83:0:17 | 91 |
14 | Me | 0.05 | Hoveyda II | 5 | 100 | 16.0 | 100 | 63:0:37 | 77 |
Calculated from 1H NMR of the crude.
Isolated yield for the inseparable mixture.
ND = not determined.