Table 3.

Asymmetric Epoxidation of cis- and Trisubstituted Olefins by Ketone 3d^a

entry	substrate	conv. (yield) (%)b	ee (%)	config.g
1		100c(60)	85e	(−)-(1R,2S)3a
2		89d(87)	84f	(+)-(3R,4R)3a
3		99c(89)	80e	(−)-(S,S)2b,3c,d
4		88d(56)	90f	(+)-(1R, 2S)2b

^aAll reactions were carried out with substrate (0.2 mmol), ketone 3d (0.06 mmol for entry 1, 0.04 mmol for entries 2, 3, and 4), Oxone (0.32 mmol), and K₂CO₃ (1.344 mmol) in DME/DMM (3:1, v/v; 3.0 mL) and buffer (0.1 M K₂CO₃-AcOH in 4 × 10⁻⁴ M aqueous EDTA, pH 9.3; 2 mL); For entries 1, 3, and 4, the reaction was carried out at −10 °C for 4 h; For entry 2, the reaction was carried out at 0 °C for 12 h.

^bIsolated yield.

^cThe conversion was determined by GC (B-DM column).

^dThe conversion was determined by ¹H NMR.

^eThe ee was determined by chiral GC (B-DM column).

^fThe ee was determined by chiral HPLC (Chiracel OD column).

^gThe absolute configurations were determined by comparing the measured optical rotations and GC trace with reported ones.