Synthesis of (R)- and (S)-2,3-Methanovaline from (2S)-N-Benzoyl-2-tert-butyl-4-methylene-1,3-oxazolidin-5-one

Article abstract of DOI:10.1016/S0040-4039(00)73864-0

The reaction of (2S)-N-benzoyl-2-tert-butyl-4-methylene-1,3-oxazolidin-5-one (9) with isopropylidenetriphenylphosphorane at room temperature gives the corresponding cis and trans spirocyclopropane derivatives 10 in ca. 1:1 ratio.After separation of both diastereomers, by recrystallization and flasch chromatography, and further acid hydrolysis, enantiomerically pure (R)- and (S)-2,3-methanovaline 11 are obtained.