Direct synthesis of ß-hydroxy-α-amino acids via diastereoselective decarboxylative aldol reaction.

A straightforward metal-free synthesis of anti-ß-hydroxy-α-amino acids is described. The organic base-mediated decarboxylative aldol reaction of cheap, readily available α-amidohemimalonates with various aldehydes afforded under very mild conditions anti-ß-hydroxy-α-amido esters in high yields and complete diastereoselectivity. Simple one-pot subsequent transformations enabled the corresponding anti-ß-hydroxy-α-amino acids or in a few examples their syn diastereomers to be obtained directly using epimerization conditions.