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. 2023 Jun 21;14(29):7936–7943. doi: 10.1039/d3sc01240a

Substrate scope for the asymmetric intramolecular 1,3-dipolar cycloaddition.

graphic file with name d3sc01240a-u3.jpg
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