Table 3.
Aziridine Substrate Scope for Tryptamine Synthesisa
| ||||
|---|---|---|---|---|
| entry | aziridine | time (h) | yield (%)b | ee (%)c |
| 1 |
|
48 | 88 | 97 |
| 2 |
|
72 | 81 | 98 |
| 3 |
|
48 | 79 | 94 |
| 4 |
|
72 | 62 | 97 |
| 5 |
|
48 | 73 | 95 |
| 6 |
|
48 | 64 | 93 |
| 7 |
|
120 | 53 | 91 |
| 8 |
|
168 | 25 | 53 |
Reaction conditions: aziridine (0.2 mmol), 2-methylindole (0.8 mmol), catalyst 9 (0.02 mmol), and 100 mg of 4 Å powdered molecular sieves in α,α,α-trifluorotoluene (1 mL) were heated to 40 °C for the time indicated.
Isolated yield from two or more runs.
Determined by HPLC.