Table 11.
Asymmetric aza-Michael addition reaction catalyzed by phase-transfer catalyst.
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| 53 | Conditionsa | R | Yield (%) | ee [%] | |||
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| A | B | A | B | A | B | ||
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| a | A | B | Ph | 91 | 90 | 90 | 93 |
| b | A | B | 4-Me-C6H4 | 93 | 90 | 90 | 91 |
| c | A | B | 4-BrC6H4 | 91 | 89 | 91 | 94 |
| d | A | B | 3-FC6H4 | 70 | 62 | 90 | 93 |
| e | A | B | 4-TBSOC6H4 | 94 | 92 | 92 | 95 |
| f | A | B | 2-naphthyl | 85 | 70 | 90 | 91 |
| g | A | B | 2-thienyl | 93 | 81 | 90 | 94 |
| h | A | B | 2-furyl | 90 | 82 | 90 | 93 |
| i | A | B | (CH3)2CHCH2 | 95 | 99 | 77 | 82 |
| j | A | B | t-Bu | 97 | 99 | 79 | 83 |
aConditions A: cat. (0.05 mol %) at rt or 0 °C, conditions B: cat. (1 mol %) at 0 °C.