Enantioselective Synthesis of (R)- and (S)-α-Aminoacids using (6S)- and (6R)-6-Methyl-morpholine-2,5-dione Derivatives

Article abstract of DOI:10.1016/0957-4166(95)00435-1

The alkylation of both 3 and 4 gives exclusively the trans derivatives 5 and 6, respectively, with >98% diastereoselectivity. Cleavage of the morpholine-2,5-dione ring of 5 and 6 leads to enantiomerically pure (S)- and (R)-α-aminoacids, respectively. The configurations of stereogenic centers introduced on 3, 4, 5 and 6 have been assigned on the basis of the ¹H-NMR data, conformational analysis and nOe measurements.