Table 3. Palladium-catalyzed [3+2] reactions of N-Boc iminesa.
| |||||
|---|---|---|---|---|---|
|
| |||||
| entry | substrate | product | temp (°C) | % yield | % ee |
| 1 |
|
|
45 | 98 | 87 |
| 4 | 84 | 91 | |||
| 2 |
|
|
4 | 80 | 92 |
| 3 |
|
|
4 | 83 | 86 |
| −15 | 73 | 90 | |||
| 4 |
|
|
4 | 94 | 93 |
| 5 |
|
|
4 | 91 | 90 |
| 6 |
|
|
4 | 96 | 91 |
| 7 |
|
|
4 | 93 | 85 |
| −15 | 94 | 86 | |||
| 8 |
|
|
4 | 73 | 84 |
| 9 |
|
|
4 | 86 | 84 |
| 10b |
|
|
4 | 86 | 85 |
| 11 |
|
|
4 | 71 | 88 |
| −15 | 65 | 90 | |||
| 12 |
|
|
4 | 81 | 83 |
| 13 |
|
|
4 | 75 | 86 |
| 14 |
|
|
4 | 71 | 91 |
| 15 |
|
|
4 | 74 | 88 |
| −15 | 60 | 90 | |||
| 16 |
|
|
4 | 74 | 70 |
| 17 |
|
|
4 | 88 | 72 |
| 18 |
|
|
4 | 43 | 22 |
All reactions were performed at 0.2 M in toluene with 5 mol% Pd(dba)2, 10 mol% ligand, 1.6 equiv 1, and stirred for 4 hours. Yields are isolated values; ee's were determined by chiral HPLC or chiral GC.
Reaction performed with 2.5 mol% Pd(dba)2 and 5 mol% L12.