The highly enantiocontrolled functionalization of a 2-oxazolone heterocycle by intramolecular radical-based addition. A chiral synthon for 2- amino alcohols which contain three contiguous stereocenters

Article abstract of DOI:10.1016/S0040-4039(98)01515-9

The intramolecular Ru(II)-catalyzed radical addition of the 2,2- dichloroacyl pendant group to the 2-oxazolone moiety followed by reductive dechlorination with (TMS)₃SiH provides an effective tool for the formation of the chiral 2-amino alcohol synthon in a completely regio- and stereocontrolled manner. The prepared synthon is useful in the preparation of isomers of unusual amino hydroxy acids including the key component of bleomycins.