Stereoselective synthesis of β-hydroxy-α-amino acids β-substituted with non-aromatic heterocycles

We have stereo selectively synthesised P-hydroxy-a-amino acids beta-substituted with non-aromatic heterocycles by means of a condensation reaction between enantiomerically pure heterocyclic aldehydes and the (R)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (Schollkopf's reagent) as a chiral auxiliary. The stereocontrolled addition gave mixtures of diastereoisomers whose steric configurations were assigned on the basis of spectroscopic data and X-ray analysis. Upon controlled hydrolysis, the adducts were transformed into the corresponding methyl esters of beta-hydroxy-beta-heterocyclic substituted a-amino acids. (c) 2007 Elsevier Ltd. All rights reserved.