152982-56-4Relevant articles and documents
Synthesis of (R)- and (S)-2,3-Methanovaline from (2S)-N-Benzoyl-2-tert-butyl-4-methylene-1,3-oxazolidin-5-one
Chinchilla, Rafael,Najera, Carmen,Garcia-Granda, Santiago,Menendez-Velazquez, Amador
, p. 5799 - 5802 (1993)
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.