Substrate scope of aldimine estersa.
| ||||||
|---|---|---|---|---|---|---|
| Entry | R | 3 | Yieldb (%) | drc (endo : exo) | Dc (%) | eec (%) |
| 1 | p-ClC6H4 | 3a | 92 | >20 : 1 | 96 | 99 |
| 2 | o-ClC6H4 | 3b | 74 | 14 : 1 | 95 | 99 |
| 3 | m-ClC6H4 | 3c | 67 | >20 : 1 | 95 | 99 |
| 4 | p-BrC6H4 | 3d | 95 | 17 : 1 | 96 | 99 |
| 5 | p-FC6H4 | 3e | 90 | 13 : 1 | 96 | 99 |
| 6 | Ph | 3f | 89 | 19 : 1 | 94 | 99 |
| 7 | p-MeC6H4 | 3g | 88 | 17 : 1 | 96 | 99 |
| 8 | o-MeC6H4 | 3h | 57 | 19 : 1 | 96 | 99 |
| 9 | m-MeC6H4 | 3i | 71 | 13 : 1 | 96 | 97 |
| 10 | p-MeOC6H4 | 3j | 90 | 13 : 1 | 94 | 99 |
| 11 | 1-Naphthyl | 3k | 63 | 13 : 1 | 93 | 99 |
| 12 | 2-Naphthyl | 3l | 56 | 17 : 1 | 95 | 99 |
| 13 | 2-Furyl | 3m | 66 | 9 : 1 | 96 | 98 |
| 14 | Cyclohexyl | 3n | 45 | >20 : 1 | 92 | 95 |
| 15d | p-ClC6H4 | 3a | 95 | >20 : 1 | 96 | 99 |
a
All reactions were carried out with 0.2 mmol of 1, 0.3 mmol of 2, 0.01 mmol of Cu(i)/(S)-L1, and 0.2 mmol of Et3N in 2 mL of DCM and 0.1 mL of D2O for 3–6 h, see the ESI for details.
b
Yields refer to isolated yields of deuterated products.
c
The dr value was determined by crude 1H NMR. D refers to D-incorporation percentages based on the calculations described in the ESI. The ee value was determined by HPLC analysis.
d
1.0 mmol scale.