(4R)-4-[(1R)-1,2-dihydroxyethyl]-1-[(1R)-1-phenylethyl]pyrrolidin-2-one

Abstract

The title compound, C14H19NO3, was obtained as one of the two isomers of a Sharpless asymmetric dihydroxylation reaction of (1S)-1-[(1R)-1-phenylethyl]-4-vinylpyrrolidin-2-one. The absolute stereochemistry of this isomer was determined from the known stereochemistry (R) at the bridge C atom between the phenyl and pyrrolidine rings. The molecules form one-dimensional tapes along the b axis via hydrogen bonding between the carbonyl O atom and the alcohol groups of neighbouring molecules. These assemble into sheets via interdigitative stacking of the phenyl rings and C-H center dot center dot center dot O interactions.