Substrate scope of aldimine estersa.
| ||||||
|---|---|---|---|---|---|---|
| Entry | R | R′ | 3 | drb | Yield (%)c | ee (%)d |
| 1 | p-ClC6H4 | Me | 3a | 18 : 1 | 67 | 99 |
| 2 | p-BrC6H4 | Me | 3b | 19 : 1 | 68 | 99 |
| 3 | p-FC6H4 | Me | 3c | 17 : 1 | 64 | 99 |
| 4 | m-ClC6H4 | Me | 3d | 14 : 1 | 62 | 99 |
| 5 | m-BrC6H4 | Me | 3e | 16 : 1 | 70 | 98 |
| 6 | Ph | Me | 3f | 15 : 1 | 68 | 99 |
| 7 | p-MeC6H4 | Me | 3g | 12 : 1 | 60 | 97 |
| 8 | p-MeOC6H4 | Me | 3h | 18 : 1 | 66 | 99 |
| 9 | m-MeC6H4 | Me | 3i | 15 : 1 | 58 | 99 |
| 10 | m-MeOC6H4 | Me | 3j | 16 : 1 | 61 | 99 |
| 11 | o-MeC6H4 | Me | 3k | 11 : 1 | 63 | 99 |
| 12 | o-ClC6H4 | Me | 3l | 15 : 1 | 66 | 99 |
| 13 | o-BrC6H4 | Me | 3m | 15 : 1 | 64 | 99 |
| 14 | 2-thienyl | Me | 3n | 14 : 1 | 58 | 99 |
| 15 | 2-furyl | Me | 3o | 10 : 1 | 55 | 99 |
| 16 | n-Pr | Me | 3p | 11 : 1 | 44 | 99 |
| 17 |
|
3q | 10 : 1 | 62 | 99 | |
| 18 | p-ClC6H4 | Et | 3r | 20 : 1 | 66 | 99 |
| 19 | p-ClC6H4 | n-Pr | 3s | 20 : 1 | 63 | 99 |
| 20e | p-ClC6H4 | Allyl | 3t | 20 : 1 | 66 | 99 |
| 21 | p-ClC6H4 | CH2Ot-Bu | 3u | 20 : 1 | 65 | 99 |
| 22 | p-ClC6H4 | CH2CH2CO2Me | 3v | 19 : 1 | 58 | 99 |
| 23 | p-ClC6H4 | H | 3w | 9 : 1 | 54 | 99 |
| 24f | p-ClC6H4 | Me | 3a | 15 : 1 | 68 | 99 |
a
All reactions were carried out with 0.30 mmol 1 and 0.20 mmol 2a in 2 mL of DCE. Cu(i) = Cu(MeCN)4BF4. Ir(i) = [Ir(cod)Cl]2.
b
dr was determined by the 1H NMR of the crude reaction mixture.
c
Isolated yields of the overall two steps.
d
ee was determined by chiral HPLC analysis.
e
Ethyl aldimine ester.
f
1.0 mmol scale.