A novel one-pot asymmetric synthetic method for the direct conversion of bromoacetates
into highly substituted hydantoins has been developed. Both enantiomers of 1,3,5-trisubstituted
hydantoins were conveniently synthesized through a dynamic kinetic resolution of bromoacetates
derived from either ethyl l-lactate or diacetone-d-glucose. The sequential three-component reaction permitted the preparation of (R)- or (S)-1,3,5-trisubstituted hydantoins in yields of 77–51% with enantiomeric ratios of
up to 95:5.
Key words
hydantoins - one-pot reaction - asymmetric synthesis - kinetic resolution - chiral
auxiliaries - bromoacetates