Table 5.
Copper-catalyzed ACA of aryl aluminum reagents to β-substituted cyclic enones.[a]
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|---|---|---|---|---|---|---|---|
| Entry | Substrate | Ar | T [°C] | t [h] | Yield [%][b] | e.r.[c] | ee [%][c] |
| 1 | 6c | C6H5 | −50 | 48 | 66 | 86:14 | 72 |
| 2 | 6c | oMeC6H4 | −15 | 48 | 85 | 99:1 | 98 |
| 3 | 6c | pOMeC6H4 | −50 | 48 | 67 | 85.5:14.5 | 71 |
| 4 | 6c | oOMeC6H4 | −15 | 48 | 55 | 97.5:2.5 | 95 |
| 5 | 8a | C6H5 | −30 | 36 | 71 | 95:5 | 90 |
| 6 | 8a | oMeC6H4 | +4 | 42 | 49 | 98:2 | 96 |
| 7 | 8a | pOMeC6H4 | −50 | 36 | 61 | 92:8 | 84 |
| 8 | 8a | pCF3C6H4 | −30 | 36 | 52 | 93:7 | 86 |
| 9 | 8a | oOMeC6H4 | +4 | 48 | 60 | 88:12 | 83 |
See Table 2. [c] Determined by chiral GLC or HPLC analysis (see the Supporting Information for additional details).
