STEREOSELECTIVE SYNTHESIS OF BETA-HOMOTHREONINE AND 3-AMINO SUBSTITUTED CARBOHYDRATES

Both diastereomers of beta-homothreonine derivatives and other precurs ors of 3-amino substituted carbohydrates together with stereoselective ly in position 2 deuterated analogues have been synthesized by 1,4-add ition of homochiral nitrogen nucleophiles to gamma-alkoxy enoates. The product distribution of the 1,4-addition of lithium amides strongly d epends on the nature of the substrate. The configuration can in one ca se be controlled by the reagent irrespective of the substrate stereoch emistry, in other cases the topicity of the addition is complementary to published results. (C) 1998 Elsevier Science Ltd. All rights reserv ed.