DIASTEREOSPECIFIC ETHERIFICATION AND DIASTEREOSELECTIVE MONOBROMINATION OF (R)-(-)-1-(2-HYDROXY-1-PHENYLETHYL)-3,4-DIHYDROPYRIDIN-2(1H)-ONE

摘要

A one-pot diastereospecific etherification and diastereoselective monobromination with bromine or N-bromosuccinimide (NBS) of the endocyclic enamide (R)-(-)-1-(2-hydroxy-1-phenylethyl)-3,4-dihydropyridin-2(1H)-one 1 is described. The enantiopure 8-bromo-3-phenyltetrahydro-2H-oxazolo[3,2-a]pyridin-5(3H)-ones trans-2 and cis-2 were obtained in good yield, fully characterized and its relative stereochemistry was unambiguously assigned via single-crystal X-ray structure.