Table 1.
Effect of catalyst, additives and conditions on the tandem Z-selective metathesis – dihydroxylation reaction.
| |||||
|---|---|---|---|---|---|
| Entry | Ru | Acid | Changes from standard | Yield 6a (anti)[a] | Yield (syn) |
| 1 | Ru-2 | CeCl3 | none | 5 | 40 |
| 2 | Ru-3 | CeCl3 | none | 56 | 12 |
| 3 | Ru-4 | CeCl3 | none | 68 | 3 |
| 4 | Ru-4 | CeCl3 | No static vacuum | 49 | 4 |
| 5 | Ru-4 | CeCl3 | nBu4NCl (10 mol%) during dihydroxylation | 62 | 5 |
| 6 | Ru-4 | CeCl3 | Ethyl vinyl ether (1 eq) after metathesis step | 47 | 2 |
| 7 | Ru-4 | CeCl3 | 5 mol% Ru-4 | 54 | 7 |
| 8 | Ru-4 | CeCl3 | 30 mol% CeCl3 | 60 | 4 |
| 9 | Ru-4 | None | none | 31 | 1 |
| 10 | Ru-4 | H2SO4 | none | 56 | 5 |
| 11 | Ru-4 | YbCl3 | none | 61 | 3 |
[a]
Determined by integration of the crude 1H NMR spectrum using mesitylene as an internal standard.