Molecules, Volume 2, Issue 6

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Isomerisations of epoxides to allylic alcohols have been effected by strong non-nucleophilic bases such as lithium dialkylamides.[...]

The reaction and the product ratio shown in the scheme was reported [1] [...]

To a solution of [3R*,5S8,6S*]-1,7-dioxaspiro[5.5]undecane-3,5-diol (50 mg, 0.27 mmol) in dichloromethane (5.0 ml), was added triethylamine (56 mg, 0.55 mmol), 4-dimethylaminopyridine (~1 mg), and 3,5-dinitrobenzoyl chloride (64 mg, 0.28 mmol) and th...

To a solution of [3R*,5S8,6S*]-1,7-dioxaspiro[5.5]undecane-3,5-diol (50 mg, 0.27 mmol) in dichloromethane (5.0 cm3), was added triethylamine (60 mg, 0.59 mmol), 4-dimethylaminopyridine (~1 mg), 3,5-dinitrobenzoyl chloride (136 mg, 0.59 mmol) and the...

A solution of [3R*,4R*,5S*,6S*]-3,4-epoxy-1,7-dioxaspiro[5.5]undecan-5-ol (1) (561 mg, 3.01mmol) in dry tetrahydrofuran (30 ml) under a nitrogen atmosphere was cooled to 0 deg.C in an ice/water bath.[...]

The reaction and the product ratio shown in the scheme was reported [1].[...]

To a solution of [4R*,5R*,6S*]-1,7-dioxaspiro[5.5]undecane-4,5-diol (1) (50 mg, 0.27 mmol) in dichloromethane (10 ml) was added triethylamine (100 mg, 0.99 mmol), acetic anhydride (67 mg, 0.66 mmol) and 4-dimethylaminopyridine (3 mg).[...]

To a solution of [3S*,5S*,6S*]-1,7-dioxaspiro[5.5]undecane-3,5-diol (1) [1] (33 mg, 0.17 mmol) in dichloromethane (10 ml) was added triethylamine (54 mg, 0.53 mmol), acetic anhydride (34 mg, 0.34 mmol) and 4-dimethylaminopyridine (3 mg).[...]

The general part of the experimental section [1] has been presented elsewhere.[...]