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1 New address: P. Krasik, Torcan Chemical Ltd. P.O. Box 308, 110 Industrial Parkway North, Aurora, Ontario, L4G 3H4, Canada; e-mail: pavel.krasik@torcan.com.
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17 The competition experiment was carried out as follows: Cu(OTf)2 (2 mol%) was dissolved in CH2Cl2 (1 mL) and dry acetone (1.5 mL, 10 equiv). The reaction mixture was cooled to -20 °C, a mixture of styrene oxide (1 mmol) and 1-butene oxide (1 mmol) was added dropwise. The reaction mixture was stirred for 1 h at -20 °C, poured onto sat. aq NaHCO3 solution (5 mL). CH2Cl2 (10 mL) was added and the organic layer was separated. The reaction mixture was analyzed by 1H NMR. Complete conversion to 1,3-dioxolane was detected for styrene oxide. 1-Butene oxide remains unchanged.
18 Typical procedure for epoxide-opening with carbonyl compounds is as follows: Cu(OTf)2 (2 mol%) was dissolved in CH2Cl2 (1 mL) and dry acetone (1.5 mL, 10 equiv). The reaction mixture was cooled to -20 °C, styrene oxide (2 mmol) was added dropwise. The reaction mixture was stirred for 1 h at -20 °C, poured onto sat. aq NaHCO3 solution (5 mL). CH2Cl2 (10 mL) was added and the organic layer was separated. The product was purified by flash chromatography (10% EtOAc in hexane) to give 2,2-dimethyl-4-phenyl-1,3-dioxolane in 95% yield. 1H NMR (400 MHz, CDCl3): δ = 1.52 (s, 3 H), 1.58 (s, 3 H), 3.72 (dd, J = 8.2, 8.1 Hz, 1 H), 4.34 (dd, J = 8.1, 6.3 Hz, 1 H), 5.10 (dd, J = 7.9, 6.3 Hz, 1 H), 7.20-7.60 (m, 5 H). 13C NMR (400 MHz, CDCl3): δ = 139.48, 128.99, 128.50, 126.68, 110.15, 78.40, 72.14, 27.06, 26.45.
19 For all compounds the physical data corresponded to that published earlier.
20 Conditions: 5 mol% of Cu(OTf)2, -80 °C, 178 h.