Scope of anti-selective Michael addition.
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|---|---|---|---|---|---|---|---|
| Entry | 1 | 2: R2 | T (d) | anti-5 | Yielda (%) | drb | eec (%) |
| 1 | 1a | 2a: 4-ClC6H4 | 2.5 | anti-5a | 99 | 15 : 1 | 95 |
| 2 | 1a | 2b: 3-ClC6H4 | 2.5 | anti-5b | 99 | 14 : 1 | 95 |
| 3 | 1a | 2c: 2-FC6H4 | 3 | anti-5c | 95 | 8 : 1 | 91 |
| 4 | 1a | 2d: Ph | 5 | anti-5d | 90 | 20 : 1 | 96 |
| 5 | 1a | 2e: 4-MeC6H4 | 5 | anti-5e | 91 | 25 : 1 | 95 |
| 6 | 1a | 2f: 2-naphthyl | 5 | anti-5f | 99 | 22 : 1 | 95 |
| 7 | 1a | 2g: 2-thienyl | 5 | anti-5g | 97 | 20 : 1 | 97 |
| 8d | 1a | 2h: (E)-PhCH CH | 5 | anti-5h | 78 | 6 : 1 | 90 |
| 9 | 1b | 2a: 4-ClC6H4 | 1.5 | anti-5v | 89 | 10 : 1 | 93 |
| 10 | 1c | 2a: 4-ClC6H4 | 3 | anti-5w | 86 | 17 : 1 | 95 |
| 11 | 1d | 2a: 4-ClC6H4 | 2 | anti-5x | 91 | 30 : 1 | 96 |
| 12 | 1e | 2a: 4-ClC6H4 | 4 | anti-5y | 99 | 14 : 1 | 94 |
| 13e | 1c | 2m: CF3 | 3.5 | anti-5q | 88 | 11 : 1 | 94 |
| 14f | 1d | 2m: CF3 | 3.5 | anti-5r | 91 | 19 : 1 | 94 |
| 15e | 1d | 2n: CF2H | 3 | anti-5s | 93 | 7 : 1 | 94 |
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Isolated yield.
Determined by 1H NMR analysis of the crude mixture.
Determined by HPLC analysis.
10 mol% 4b.
20 mol% 4b and 20 mol% K2HPO4·3H2O.
10 mol% 4b and 10 mol% K2HPO4·3H2O.
20 mol% 4b.