CYCLOHEXANONE, 3,5-DIMETHYL-, (3R,5S)-REL-

反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 2-trimethylsilyl-1,3-dithiane (30.1 g, 0.16 mol) in THF (250 mL) at 0° C. under an argon atmosphere was added a solution of n-butyl lithium (2.5 M in hexanes, 64 mL, 0.16 mol) and the mixture was cooled to −78° C. A solution of cis-3,5-dimethyl cyclohexanone (10 g, 0.079 mol) in THF (30 mL) was added over 10 min. After 3.5 h the reaction mixture was quenched with saturated aqueous NH4Cl solution (100 mL). The aqueous phase was extracted with EtOAc (100 mL×4) and the combined organic layers were dried (MgSO4) and were evaporated. The reaction by-products were removed by vacuum distillation to yield the desired product (16.6 g, 92%). MH+229 After 3.5 h the reaction mixture was quenched with saturated aqueous NH4Cl solution (100 mL) The aqueous phase was extracted with EtOAc (100 mL×4) the combined organic layers were dried (MgSO4) were evaporated The reaction by-products were removed by vacuum distillation

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A solution of 3,5-dimethyl-2-cyclohexenone (2.0 g, 16.1 mmol) in 2-propanol (32 ml) was hydrogenated over 5% palladium on charcoal (200 mg) at room temperature and 103 kPa (14.7 psi) for 4 hours, then diluted with 1:1 hexane:ether (150 ml) and filtered using a filter aid. The filtrate was evaporated under reduced pressure to provided the substantially stereochemically pure title compound (1.56 g) as a yellow oil. 13C NMR spectroscopy revealed a cis:trans ratio of 150:3. ether (150 ml) and filtered The filtrate was evaporated under reduced pressure