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. 2020 Jan 14;11(8):2121–2129. doi: 10.1039/c9sc06089h

Scope of the enantioselective oxygenation of 3-benzylquinolone derivatives 2 catalysed by the chiral manganese porphyrin catalyst 1.

graphic file with name c9sc06089h-u1.jpg
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
a

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).

b

All yields refer to isolated material. Yields in brackets are based on reisolated starting material 2.

c

Enantiomeric excess (% ee) as determined by HPLC analysis on a chiral stationary phase.