Table 2.
Substrate Scope of the Enantioselective Decarboxylative Allylic Alkylation of Enaminonesa
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|---|---|---|---|---|---|
| entry | product | R1 | R2 | yield (%)b | ee (%)c |
| 1 | 2a | Me | H | 95 (93)d | 99 (98)d |
| 2 | 2b | Et | H | 99 | 98 |
| 3 | 2c | CH2OTBS | H | 96 | 99 |
| 4 | 2d | CH2CH2OTBS | H | 93 | 99 |
| 5 | 2e | CH2CH2CO2Me | H | 98 | 97 |
| 6 | 2f | CH2CH2C(O)Me | H | 90 | 94 |
| 7 | 2g | CH2CH2CN | H | 99 | 94 |
| 8 | 2h | Bn | H | 95 | 96 |
| 9 | 2i | p-(OMe)Bn | H | 99 | 95 |
| 10 | 2j | p-(CF3)Bn | H | 87 | 92 |
| 11 | 2k | Me | Me | 92 | 99 |
| 12 | 2l | Me | Cl | 58 | 99 |
Conditions: β-ketoester (0.47 mmol), Pd2(dmdba)3 (5.0 mol %), (S)-t-BuPHOX (12.5 mol %), EtOAc (14 mL), 40 °C, 9 h.
Isolated yield.
Determined by analytical chiral SFC. See Supporting Information for details.
Conditions: β-ketoester (12.3 mmol), Pd2(dmdba)3 (0.5 mol %), (S)-t-BuPHOX (1.3 mol %), EtOAc (37 mL), 40 °C.
