(S)-tert-butyl 4-((R)-2-(allyloxymethyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate → (S)-tert-butyl 2,2-dimethyl-4-(((R,Z)-2,3,4,7-tetrahydrooxepin-3-yl)methyl)oxazolidine-3-carboxylate

Participants

Reaction Steps

To a solution of (S)-tert-butyl 4-((R)-2-(allyloxymethyl)pent-4-enyl)-2,2-dimethyloxazolidine-3-carboxylate (700 mg, 2.06 mmol, 1 eq) in anhydrous CH2Cl2 was added Grubbs catalyst 2nd generation ((1,3-Bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(phenylmethylene)(tricyclohexylphosphine)ruthenium) (173 mg, 0.21 mol, 0.1 eq). The resulting mixture was stirred and heated to reflux for 4 h. The solvent was removed under reduced pressure to afford the crude product. It was purified by column chromatography on silica gel (PE:EA=100:1) to give (S)-tert-butyl 2,2-dimethyl-4-(((R,Z)-2,3,4,7-tetrahydrooxepin-3-yl)methyl)oxazolidine-3-carboxylate (563 mg, 88%).

Provenance & Evidence