Table 2.
Allylation of 1-methyl-imidazolidin-2-one (1) as a function of allylic alcohol catalyzed by a mixture of (2)AuCl (5 mol %) and AgSbF6 (5 mol %) in dioxane (Nuc = N-methyl-imidazolidin-2-one).
| entry | alcohol | major product | conda | yield (%)b | γ/α ratioc | E/Z ratioc |
|---|---|---|---|---|---|---|
| 1 |
|
|
A | 99 | >25:1 | — |
|
|
|||||
| 2 | R = Me | 4 | B | 91 | >25:1 | 2.4:1 |
| 3 | R = Ph | 5 | B | 94 | >25:1 | 6.7:1 |
|
|
|||||
| 4 | R = Me | 6a | A | 100 | >25:1 | — |
| 5 | R = –(CH2)5– | 7 | A | 100 | >25:1 | — |
| 6 |
|
|
C | 85 | >25:1 | — |
| 7 |
|
|
D | 97 | — | — |
| 8 |
|
|
A | 100 | >25:1 | 3.7:1 |
| 9 |
|
|
A | 100 | — | >25:1 |
| 10 |
|
|
A | 100 | >25:1 | 4.3:1 |
| 11 |
|
|
D | 85 | <1:25 | >25:1 |
| 12 |
|
|
B | 100 | 1:12 | — |
a
Conditions: A = 2 equiv alcohol, 60 °C, 24 h; B = 1 equiv alcohol, 60 °C, 24 h; C = 2 equiv alcohol, 25 °C, 36 h; D = 2 equiv alcohol, 100 °C, 48 h.
b
Isolated material of >95% purity.
c
Determined by 1H NMR analysis of the purified reaction mixture.