Table 3.
| ||||
---|---|---|---|---|
entry | substrate | amine | % yieldb | er |
1 2c |
98 95 |
>99:1 99:1 |
||
3 | 4b | 88 | 95:5 | |
4 | 4b | 90 | 95:5 | |
5 | 4b | 47 | 89:11 | |
6 | 4b | 63 | >99:1 | |
7 | 4b | 82 | 97:3 | |
8 | 56 | 97:3 | ||
9 | 4c | 59 | >99:1 | |
10 | 77 | 98:2 |
Conditions: Reactions were conducted on a 0.1 mmol scale using 1.0 equiv 4, 1.2 equiv amine, 1.4 equiv LiOtBu, 4 mol % Pd(OAc)2, 10 mol % (S)-tBu-PHOX, toluene (0.1 M), 95 °C, 3–16 h.
Isolated yields (average of two or more experiments).
The reaction was conducted on a 1.0 mmol scale.