Scope of the enantioselective oxygenation of 3-benzylquinolone derivatives 2 catalysed by the chiral manganese porphyrin catalyst 1.
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Entrya | 2 | X | R | 3 b [%] | % eec |
1 | 2a | H | 4′-Me | 60 (80) | 96 |
2 | 2b | H | 3′-Me | 58 (82) | 99 |
3 | 2c | H | 2′-Me | 64 (92) | 97 |
4 | 2d | H | 3′,4′-Me2 | 59 (68) | 92 |
5 | 2e | H | H | 61 (84) | 95 |
6 | 2f | H | 4′-OMe | 53 (74) | 93 |
7 | 2g | H | 4′-F | 53 (60) | 91 |
8 | 2h | H | 4′-Cl | 18 (62) | 98 |
9 | 2i | H | 3′-CF3 | 26 (54) | 92 |
10 | 2j | 6-Me | 4′-Me | 60 (71) | 98 |
11 | 2k | 7-Me | 4′-Me | 53 (65) | 96 |
All reactions were conducted at a iodosobenzene concentration of 10 mM in dichloromethane employing 1.0 equiv. of PhIO (60 μmol), 3.0 equiv. of 2 (180 μmol) and 1.5 mol% of 1 (0.9 μmol).
All yields refer to isolated material. Yields in brackets are based on reisolated starting material 2.
Enantiomeric excess (% ee) as determined by HPLC analysis on a chiral stationary phase.