A facile and stereocontrolled synthesis of syn-α-alkyl α-hydroxy β-amino acids

Article abstract of DOI:10.1016/S0040-4039(99)01772-4

The diastereoselective synthesis of syn-α-alkyl α-hydroxy β-amino acids 4a-h was easily accomplished by reaction of the sodium dianion of the corresponding anti α-alkyl β-benzoylamino acid methyl esters with iodine. The intermediate α-iodo derivatives spontaneously afforded cis-oxazolines which, upon hydrolysis, provided the desired products, with diastereoselectivities up to 99:1.