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Scope of hydrogen-bond-promoted acetyl phosphonate aldol reaction.
 | |||||
|---|---|---|---|---|---|
| Entry | R | Product | Yield [%] | d.r. (anti/syn) | ee [%] |
| 1 | Me | 15 a | 73 | 97:3 | 95 |
| 2 | Et | 15 b | 51 | 99:1 | 89 |
| 3 | Bn | 15 c | 66 | 99:1 | 91 |
| 4 | iBu | 15 d | 52 | 99:1 | 96 |
| 5 | OMe | 15 e | 61 | 99:1 | 95 |
| 6 | OPh | 15 f | 82 | 99:1 | 99 |
| 7 | OPMP | 15 g | 81 | 99:1 | 99 |
| 8 | SMe | 15 h | 52 | 99:1 | 98 |
| 9 | Cl | 15 i | 77 | 99:1 | 97 |
All reaction were performed in toluene at 0.3 m acyl phosphonate and 1.5 equivalent of ketene acetal.
