Table 2.
Catalytic Enantioselective Allyl-Allyl Cross-Coupling.a
 | ||||||
|---|---|---|---|---|---|---|
| entry | substrate | product | ligand | yield | regio. | ee |
| 1 |  |
 |
A | 72 | >20:1 | 91 |
| 2 |  |
 |
A | 69 | >20:1 | 91 |
| 3 |  |
 |
A | 75 | >20:1 | 91 |
| 4 |  |
 |
A | 59 | >20:1 | 90 |
| 5b |  |
 |
A | 87 | >20:1 | 90 |
| 6 |  |
 |
A | 83 | >20:1 | 91 |
| 7 |  |
 |
A | 52 | >20:1 | 90 |
| 8 |  |
 |
A | 60 | >20:1 | 74 |
| 9c |  |
 |
A | 53 | >20:1 | 87 |
| 10 |  |
 |
A B |
35 9 |
>20:1 3:1 |
83 94 |
| 11 |  |
 |
B | 63 | 10:1 | 91 |
| 12 |  |
 |
B | 80 | 11:1 | 84 |
| 13d |  |
 |
B | 91 | >20:1 | 90 |
| 14 |  |
 |
B | 75 | >20:1 | 85 |
(a)
Unless otherwise noted, reactions employ 1.2 equivalents of allylB(pin).
(b)
Reaction with 1.5 equiv. of allylB(pin).
(c)
2.0 equiv. allylB(pin), 36h.
(d)
1.2 equivalents of Cs2CO3 added.