Scope of syn-selective Michael addition.
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|---|---|---|---|---|---|---|---|
| Entry | 1 | 2: R2 | Time (d) | syn-5 | Yielda (%) | drb | eec (%) |
| 1 | 1a | 2a: 4-ClC6H4 | 7 | syn-5a | 76 | 7 : 1 | 93 |
| 2 | 1a | 2b: 3-ClC6H4 | 8 | syn-5b | 79 | 7 : 1 | 93 |
| 3 | 1a | 2c: 2-FC6H4 | 7 | syn-5c | 73 | 9 : 1 | 95 |
| 4 | 1a | 2d: Ph | 9 | syn-5d | 85 | 9 : 1 | 96 |
| 5 | 1a | 2e: 4-MeC6H4 | 10 | syn-5e | 79 | 9 : 1 | 96 |
| 6 | 1a | 2f: 2-naphthyl | 7 | syn-5f | 81 | 8 : 1 | 93 |
| 7 | 1a | 2g: 2-thienyl | 7 | syn-5g | 85 | 10 : 1 | 96 |
| 8 | 1a | 2h: (E)-PhCH CH | 8 | syn-5h | 76 | 15 : 1 | 94 |
| 9 | 1a | 2i: (E)-4-BrC6H4CH CH | 5 | syn-5i | 70 | 13 : 1 | 93 |
| 10 | 1a | 2j: (E)-3-FC6H4CH CH | 6 | syn-5j | 68 | 12 : 1 | 92 |
| 11 | 1a | 2k: (E)-2-FC6H4CH CH | 8 | syn-5k | 81 | 12 : 1 | 94 |
| 12 | 1a | 2l: (E)-2-MeC6H4CH CH | 9 | syn-5l | 80 | 13 : 1 | 94 |
| 13d | 1b | 2h: (E)-PhCH CH | 4 | syn-5m | 88 | 12 : 1 | 90 |
| 14 | 1c | 2h: (E)-PhCH CH | 2 | syn-5n | 79 | 12 : 1 | 88 |
| 15d | 1d | 2h: (E)-PhCH CH | 4 | syn-5o | 72 | 13 : 1 | 93 |
| 16 | 1e | 2h: (E)-PhCH CH | 8 | syn-5p | 69 | 14 : 1 | 95 |
| 17e | 1c | 2m: CF3 | 3 | syn-5q | 75 | 3 : 1 | 90 |
| 18e | 1d | 2m: CF3 | 2 | syn-5r | 76 | 4 : 1 | 92 |
| 19e | 1d | 2n: CF2H | 6 | syn-5s | 52 | 2 : 1 | 87 |
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Isolated yield.
Determined by 1H NMR analysis of the crude reaction mixture.
Determined by HPLC analysis.
−20 °C.
5 Å MS was replaced by 20 mol% K2HPO4·3H2O.