[(2S,3R)-3-(phenylmethoxymethyl)oxiran-2-yl]methanol

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 10 ml CCl4, 10 ml CH3CH, and 15 ml of H2O was added 50 mg of RuCl3 --H2O and 1.00 g (5.16 mmole) of (2S-cis)-3-(benzyloxymethyl)oxirane methanol. The solution was cooled to 0° C. and 3.50 g (15.5 mmole) of H5IO6 was added in portions over 15 min with vigorous stirring. The reaction was allowed to stir vigorously for 2 hours. The mixture was poured into 100 ml of Et2O, the organic layer separated and the aqueous layer washed with 20 ml of Et2O. The combined organic layers were washed four times with 50 ml 0.1 N NaOH. The aqueous layers were combined, acidified to pH 2, and extracted three times with 50 ml Et2O. The ether layers were dried over MgSO4, filtered and evaporated to yield a pale yellow residue. the organic layer separated the aqueous layer washed with 20 ml of Et2O The combined organic layers were washed four times with 50 ml 0.1 N NaOH extracted three times with 50 ml Et2O The ether layers were dried over MgSO4 filtered evaporated to yield a pale yellow residue

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a slurry of 5.0 g of powdered 4A molecular sieves in 400 ml of dry CH2Cl2 was added 2.09 g (8.42 mmole) of Ti(Oi-Pr)4 and 2.76 g (11.8 mmole) of L(+)diisopropyl tartrate at 0° C. under argon. The mixture was allowed to stir for 10 min, cooled to -20° C., and 22.5 ml of 3.8 M tert-butyl hydroperoxide in isooctane is added slowly at -20° C. The catalyst was allowed to "age" for 30 min. A solution of 7.50 g (42.1 mmole) of Z-4-(benzyloxy)-2-buten-1-ol in 15 ml of CH2Cl2 was dried over 3A molecular sieves for 15 min and then added to the mixture at -20° C. over 10 min. The mixture was allowed to stand in a refrigerator at 2° C. for 8 days. The reaction mixture was removed from the refrigerator and 40 ml of H2O was added with stirring. After stirring for 30 min, 15 ml of 30% NaOH in saturated brine was added and the mixture was allowed to stir 60 min longer. The organic layer was separated and the aqueous layer washed twice with 50 ml of CH2Cl2. The organic layers were combined, dried over MgSO4, filtered and evaporated to afford a milky, pale yellow oil. Distillation yielded 4.80 g of a clear viscous oil, bp 132-5° C. (0.2 mm Hg). 1H NMR, δ 7.4-7.2 (m, 5), 4.58 (dd, 2, J=12, 20 Hz), 3.7 (m, 4), 3.27 (ddd, 2, J=5, 10, 15 Hz), 1.98 (t, 1, J=6 Hz). Mass Spectra; EI; M+, Calc. 194.0942, Found 194.0929. The catalyst was allowed to "age" for 30 min added to the mixture at -20° C. over 10 min to stand in a refrigerator at 2° C. for 8 days The reaction mixture was removed from the refrigerator and 40 ml of H2O was added with stirring After stirring for 30 min 15 ml of 30% NaOH in saturated brine was added to stir 60 min longer The organic layer was separated the aqueous layer washed twice with 50 ml of CH2Cl2 dried over MgSO4 filtered evaporated to afford a milky, pale yellow oil Distillation

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 10 ml CCl4, 10 ml CH3CH, and 15 ml of H2O was added 50 mg of RuCl3 --H2O and 1.00 g (5.16 mmole) of (2S-cis)-3-(benzyloxymethyl)oxirane methanol. The solution was cooled to 0° C. and 3.50 g (15.5 mmole) of H5IO6 was added in portions over 15 min with vigorous stirring. The reaction was allowed to stir vigorously for 2 hours. The mixture was poured into 100 ml of Et2O, the organic layer separated and the aqueous layer washed with 20 ml of Et2O. The combined organic layers were washed four times with 50 ml 0.1N NaOH. The aqueous layers were combined, acidified to pH 2, and extracted three times with 50 ml Et2O. The ether layers were dried over MgSO4, filtered and evaporated to yield a pale yellow residue. the organic layer separated the aqueous layer washed with 20 ml of Et2O The combined organic layers were washed four times with 50 ml 0.1N NaOH extracted three times with 50 ml Et2O The ether layers were dried over MgSO4 filtered evaporated to yield a pale yellow residue

Conditions: temp:-20.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a slurry of 5.0 g of powdered 4A molecular sieves in 400 ml of dry CH2Cl2 was added 2.09 g (8.42 mmole) of Ti(Oi-Pr)4 and 2.76 g (11.8 mmole) of L(+)diisopropyl tartrate at O'C under argon. The mixture was allowed to stir for 10 min, cooled to -20° C., and 22.5 ml of 3.8M tert-butyl hydroperoxide in isooctane is added slowly at -20° C. The catalyst was allowed to "age" for 30 min. A solution of 7.50 g (42.1 mmole) of Z-4-(benzyloxy)-2-buten-1-ol in 15 ml of CH2Cl2 was dried over 3A molecular sieves for 15 min and then added to the mixture at -20° C. over 10 min. The mixture was allowed to stand in a refrigerator at 2° C. for 8 days. The reaction mixture was removed from the refrigerator and 40 ml of H2O was added with stirring. After stirring for 30 min, 15 ml of 30% NaOH in saturated brine was added and the mixture was allowed to stir 60 min longer. The organic layer was separated and the aqueous layer washed twice with 50 ml of CH2Cl2. The organic layers were combined, dried over MgSO4, filtered and evaporated to afford a milky, pale yellow oil. Distillation yielded 4.80 g of a clear viscous oil, bp 132°-5° C. (0.2 mm Hg). 1H NMR, δ7.4-7.2 (m, 5), 4.58 (dd, 2, J=12, 20 Hz), 3.7 (m, 4), 3.27 (ddd, 2, J=5, 10, 15 Hz), 1.98 (t, 1, J=6 Hz). Mass Spectra; EI; M+, Calc. 194.0942, Found 194.0929. The catalyst was allowed to "age" for 30 min added to the mixture at -20° C. over 10 min to stand in a refrigerator at 2° C. for 8 days The reaction mixture was removed from the refrigerator and 40 ml of H2O was added with stirring After stirring for 30 min 15 ml of 30% NaOH in saturated brine was added to stir 60 min longer The organic layer was separated the aqueous layer washed twice with 50 ml of CH2Cl2 dried over MgSO4 filtered evaporated to afford a milky, pale yellow oil Distillation