Table 2. Au(i)-catalyzed intramolecular cycloisomerization of 1,6-enyne 18 a.
| |||||||||
|---|---|---|---|---|---|---|---|---|---|
| Entry | [Au] | Solvent | Conv.b (%) | rr19/20 b | Entry | [Au] | Solvent | Conv.b (%) | rr19/20b |
| 1 | 22 | CD2Cl2 | 94 | 1 : 8 | 10 | 13fa | CD2Cl2 | 98 | 1 : 10.6 |
| 2 | 3a | CD2Cl2 | 97 | 1 : 10.8 | 11 | 22 | ClCH2CH2Cl | 96 | 1 : 6.3 |
| 3 | 14a | CD2Cl2 | 95 | 1 : 9.4 | 12 | 9fa | ClCH2CH2Cl | 95 | 1 : 9.9 |
| 4 | 9aa | CD2Cl2 | >99 | 1 : 7.0 | 13 | 22 | Br(CH2)4Br | >99 | 1 : 3.8 |
| 5 | 9da | CD2Cl2 | 94 | 1 : 16.1 | 14 | 9fa | Br(CH2)4Br | >99 | 1 : 10.7d |
| 6 | 9ea | CD2Cl2 | 97 | 1 : 4.1c | 15 | 13fa | Br(CH2)4Br | >99 | 1 : 5.6f |
| 7 | 9ga | CD2Cl2 | 95 | 1 : 10 | 16 | 22 | C6H11Cl | 97 | 1 : 4.6 |
| 8 | 9fa | CD2Cl2 | 98 | 1 : 23.1d | 17 | 9fa | C6H11Cl | 73 | 1 : 7.8 |
| 9 | 9fb | CD2Cl2 | 73 | 1 : 13.7e | 18 | 13fa | C6H11Cl | 95 | 1 : 6.3 |
| |||||||||
Reactions performed on a 0.1 mmol scale. Reactions performed indifferently in situ using the appropriate ligand and [(Me2S)AuCl] or ex situ (see SI).
Determined by 1H NMR spectroscopy using an internal standard.
Contains 20% of 21.
Contains 4% of 21.
Using AgSbF6 instead of NaBArF.
Contains 48% of 21.