Table 3.
| |||||
---|---|---|---|---|---|
Entry |
Alkene +thiol |
Product |
Temp. |
Yield [%][a] |
Ratio A:B |
1 |
8+20 (1.2 equiv) |
|
rt |
80 |
1.3:1[b] |
2 |
−80 °C |
76 |
8.5:1 |
||
3 |
−120 °C |
75 |
6:1 |
||
|
|
|
|
|
|
4 |
9+20 (1.2 equiv) |
|
0 °C |
67 |
2.3:1 |
5 |
−40 °C |
95 |
1.5:1 |
||
6 |
−80 °C |
95 |
1:1.2 |
||
7 |
−120 °C |
95 |
1:1.2 |
||
|
|
|
|
|
|
8 |
10+20 (1.2 equiv) |
|
rt |
38 |
1:0[b] |
9 |
−80 °C |
92 |
1:0 |
||
|
|
|
|
|
|
10 |
11+20 (1.2–2.0 equiv) |
|
rt |
66 |
2.5:1[c] |
11 |
−80 °C |
81 |
5.5:1[d] |
[a] Combined isolated yield; [b] data are taken from Ref. 23, 6 equiv, of thiol was used; [c] 2.0 equiv of thiol was used. [d] 1.2 equiv of thiol was used.