Table 2.
(R)-P-catalyzed Asymmetric aza-MBH Reaction
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|---|---|---|---|---|
| entrya | R1 | R2 | yield (%)b | ee (%)c |
| 1 | 1b, 5-CH3 | Bn | 2b', 93 | 95 |
| 2 | 1c, 5-F | Bn | 2c', 96 | 93 |
| 3 | 1d, 5-Cl | Bn | 2d', 91 | 99 |
| 4 | 1e, 5-Br | Bn | 2e', 97 | >99 |
| 5 | 1f, 6-CH3 | Bn | 2f', 88 | 99 |
| 6 | 1g, 6-Cl | Bn | 2g', 93 | 96 |
| 7 | 1h, 6-Br | Bn | 2h', 93 | 97 |
| 8 | 1i, 7-F | Bn | 2i', 87 | 95 |
| 9 | 1j, 7-Cl | Bn | 2j', 70 | 99 |
| 10 | 1k, 7-Br | Bn | 2k', 78 | 99 |
| 11 | 1l, 7-CF3 | Bn | 2l', 70 | 94 |
| 12 | 1m, 5-Cl, 7-CH3 | Bn | 2m', 86 | >99 |
| 13 | 1n, 4-CH3 | Bn | trace | ndd |
| 14 | 1o, 4,7-Cl2 | Bn | trace | ndd |
| 15 | 1p, H | Me | 2p', 85 | 95 |
| 16 | 1q, H | Allyl | 2q', 90 | 97 |
| 17 | 1r, 5-CH3O | Bn | 2r, 83 | 90 |
| 18e | 1s, H | Bn | 2s, 86 | 70 |
| 19e | 1t, 4,7-Cl2 | Bn | trace | ndd |
1 (0.1 mmol), MVK (0.2 mmol) and catalyst (0.02 mmol) were stirred in 2 mL of chloroform within 48 h at rt.
Isolated yield.
Determined by chiral HPLC.
Not determined.
t-Bu group of Boc moiety in 1a was replaced by ethyl group.
