Table 1. Ring-closing metathesis of peptides bearing i, i + 2 olefin crosslinks.
| ||||||
Catalyst | Yield
a
(%) |
Selectivity
b
(E : Z) |
||||
9a | 9b | 9c | 9a | 9b | 9c | |
m = 1, n = 1 | m = 2, n = 1 | m = 2, n = 2 | m = 1, n = 1 | m = 2, n = 1 | m = 2, n = 2 | |
1 | 58 | 54 | 68 | 81 : 19 | 72 : 28 | 66 : 34 |
2 | 71 | 61 | 77 | 91 : 9 | 88 : 12 | 82 : 18 |
3 | 63 | 55 | 70 | 90 : 10 | 85 : 15 | 83 : 17 |
4 | 66 | 60 | 66 | 82 : 18 | 85 : 15 | 78 : 22 |
5 | 45 | 24 | 44 | 81 : 19 | n.d. | 81 : 19 |
6 | 47 | 21 | 26 | 13 : 87 | n.d. | 15 : 85 |
7 | 41 | 17 | 24 | 7 : 93 | n.d. | 5 : 95 |
aIsolated yields.
bDetermined by 1H and 13C NMR spectroscopy.