Substrate scope for the asymmetric intramolecular 1,3-dipolar cycloaddition.
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|---|---|---|---|---|---|---|---|
| Entry | Product | R1 | R2 | R3 | R4 | Yield [%] | ee [%] |
| 1 | 3a | Ph | Bn | H | H | 67 | 90 |
| 2 | 3b | p-ClC6H4 | Bn | H | H | 92 | 85 |
| 3 | 3c | m-ClC6H4 | Bn | H | H | 81 | 76 |
| 4 | 3d | o-ClC6H4 | Bn | H | H | 73 | 75 |
| 5 | 3e | Ph | o-Me benzyl | H | H | 62 | 88 |
| 6 | 3f | Ph | m-Br benzyl | H | H | 47 | 85 |
| 7 | 3g | Ph | p-Cl benzyl | H | H | 59 | 85 |
| 8 | 3h | Ph | Me | H | H | 56 | 79 |
| 9 | 3i | Ph | Bn | F | H | 75 | 94 |
| 10 | 3j | Ph | Bn | Cl | H | 76 | 97 |
| 11 | 3k | Ph | Bn | Br | H | 84 | 96 |
| 12 | 3l | Ph | Bn | Me | H | 98 | 97 |
| 13 | 3m | Ph | Bn | MeO | H | 63 | 98 |
| 14 | 3n | Ph | Bn | CF3O | H | 69 | 96 |
| 15 | 3o | Ph | Bn | H | F | 68 | 83 |
| 16 | 3p | Ph | Bn | H | Br | 82 | 80 |
| 17 | 3q | p-ClC6H4 | Bn | Me | H | 59 | 96 |
| 18 | 3r | m-ClC6H4 | Bn | Me | H | 67 | 97 |
| 19 | 3s | o-ClC6H4 | Bn | Me | H | 92 | 94 |
| 20 | 3t | Ph | o-Me benzyl | Br | H | 59 | 97 |
| 21 | 3u | Ph | o-Me benzyl | Me | H | 52 | 98 |
| 22 | 3v | Ph | m-Br benzyl | F | H | 61 | 98 |
| 23 | 3w | Ph | m-Br benzyl | Me | H | 65 | 98 |
| 24 | 3x | Ph | p-Cl benzyl | MeO | H | 58 | 99 |
| 25 | 3y | Ph | Me | F | H | 66 | 90 |
| 26 | 3z | Ph | Bn | F | F | 70 | 96 |
| 27 | 3aa | Ph | Bn | –C4H4– | 59 | 93 | |
| 28 | 3bb | p-CNC6H4 | Bn | H | H | 91 | 4 |
| 29 | 3cc | Ph | p-CN benzyl | H | H | 94 | 88 |