Scope of the enantioselective oxygenation of 3-alkylquinolones 6 to alcohol 7 and ketone 8 catalysed by the chiral manganese porphyrin catalyst 1.

Entrya	6	X	R′	7 b [%]	% eec
1	6a	H	Me	56 (90)	95
2	6b	H	Et	53 (84)	88
3	6c	H	nPr	50 (68)	86
4	6d	H	iBu	48 (96)	88
5	6e	H	iPr	48 (89)	80
6	6f	6-Me	Me	51 (93)	94
7	6g	7-Me	Me	58 (94)	96
8	6h	6,7-Me2	Me	51 (94)	95
9	6i	6-OMe	Me	21 (38)	96
10	6j	7-OMe	Me	62 (73)	95
11	6k	7-Cl	Me	34 (95)	95
12	6l	7-F	Me	42 (84)	96

^aAll reactions were conducted at a iodosobenzene concentration of 10 mM in dichloromethane employing 1.0 equiv. of PhIO (60 μmol), 3.0 equiv. of 6 (180 μmol) and 2.0 mol% of 1 (1.2 μmol).

^bAll yields refer to isolated material. Yields in brackets are based on reisolated starting material 6.

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