Stereoselective synthesis of β-homothreonine and 3-amino substituted carbohydrates

Both diastereomers of beta-homothreonine derivatives and other precursors of 3-amino substituted carbohydrates together with stereoselectively in position 2 deuterated analogues have been synthesized by 1,4-addition of homochiral nitrogen nucleophiles to gamma-alkoxy enoates. The product distribution of the 1,4-addition of lithium amides strongly depends on the nature of the substrate. The configuration can in one case be controlled by the reagent irrespective of the substrate stereochemistry, in other cases the topicity of the addition is complementary to published results. (C) 1998 Elsevier Science Ltd. All rights reserved.