Optimization of reaction conditions for Ir-catalyzed reaction of racemic allenyl carbonate 1a with benzylamine 2aa.
| |||||
|---|---|---|---|---|---|
| Entry | n | T/°C | Yield of 3aab (%) | Yield of 4aab (%) | Recovery of 1ab (%) |
| 1 | 1.5 | r.t. | 26 | 25 | — |
| 2c | 1.5 | r.t. | 24 | 27 | — |
| 3 | 2 | r.t. | 35 | 28 | — |
| 4 | 4 | r.t. | 41 | 6 | 38 |
| 5d | 4 | r.t. | 45 | 7 | 45 |
| 6d | 4 | 40 | 64 | 8 | 11 |
| 7d | 4 | 50 | 70 | 8 | — |
| 8d | 4 | 60 | 65 | 9 | — |
The reaction was conducted using 1a (0.2 mmol) in 0.4 mL of THF.
Determined by 1H NMR analysis of the crude reaction mixture using 1,3,5-trimethylbenzene as an internal standard.
7 mol% Ir pre-catalyst A was used.
The reaction was conducted using 1a (0.2 mmol) in 1.0 mL of THF.