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. Author manuscript; available in PMC: 2009 Dec 19.
Published in final edited form as: J Org Chem. 2008 Dec 19;73(24):9539–9543. doi: 10.1021/jo801576k

Table 1.

Asymmetric Epoxidation of α-Isopropylstyrene with Ketones 3a

graphic file with name nihms91447t1.jpg
entry ketone solvent conv. (%)b ee (%)b
1 3d CH3CN/DMM (1/2) 97 71
2 DME 94 81
3 DME/n-BuOH 99 76
4 1,4-dioxane 94 84
5 1,4-dioxane/DME (2/1) 99 80
6 1,4-dioxane/n-BuOH (1/1) 100 78
7 3a 91 82
8 3b 69 71
9 3c 10 nd
10 3e 100 83
11 3f 98 83
12 3g 80 52
13 3h 99 84
a

All epoxidations were carried out with the olefin (0.2 mmol), ketone 3 (0.06 mmol), Oxone (0.32 mmol), and K2CO3 (1.344 mmol) in organic solvent (3 mL) and buffer (0.1 M K2CO3/AcOH, pH 9.3; 2 mL) at −10 °C for 2 h.

b

The conversion and ee were determined by chiral GC (B-DM column).