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. Author manuscript; available in PMC: 2009 Jul 2.
Published in final edited form as: J Am Chem Soc. 2008 Jun 5;130(26):8134–8135. doi: 10.1021/ja802982h

Table 1.

Asymmetric Peroxidation of α,β-unsaturated ketones 1 with 8a

graphic file with name nihms-95245-ig0001.jpg
entry enone peroxide temp(°C) time(h) 6/3b yield(%) 6 ee (% )c 6
1d 1A 2a 23 2 91:9 nd 85
2 1A 2a 23 4 92:8 85 91
3 1B 2a 23 4 94:6 88 84
4e 1C 2a 23 4 94:6 91 90
5f 1D 2a 23 4 93:7(95:5) 86(90) 93(90)
6 1E 2a 23 4 90:10 65 91
7 1F 2a 23 4 95:5 90 89
8 1H 2a 23 4 94:6 89 87
9f 1I 2a 23 4 86:14(93:7) 64(77) 94(88)
10 1A 2b 0 16 86:14 74 94
11 1B 2b 0 12 77:23 70 92
12 1C 2b 0 12 88:12 75 92
13 1D 2b 0 16 87:13 77 95
14 1E 2b 0 12 90:10 82 96
15 1F 2b 0 24 89:11 75 94
16 1H 2b 0 24 85:15 66 96
17 1I 2b 0 24 65:35 55 97
18g 1A 2c 0 19 77:23 60 92
19g 1C 2c 0 24 86:14 70 95
20g 1D 2c 0 24 88:12 62 95
21g 1F 2c 0 17 95:5 63 95
22g 1G 2c 0 24 78:22 42 94
23g 1H 2c 0 24 95:5 60 94
a

Unless noted, reactions were run with 0.3 mmol 1, 0.36 mmol 2, see Supporting Information for details.

b

Determined by 1H NMR.

c

see Supporting Information for details.

d

Reaction was run with 20 mol% TFA in CH2CI2.

e

Absolute configuration was established as R (see Supporting Inofrmation).

f

The results in paretheses were obtained with QD-NH2.

g

Reaction was run with 20 mol% TFA.