Asymmetric Synthesis of β-Aminoacids and α-Deuterated β-Aminoacids via Conjugate Addition of Homochiral Amidocuprates
N. Sewald, K. D. Hiller, B. Helmreich
Liebigs Ann. Chem.
Conjugate addition of homochiral amidocuprates based on N-[(R)-1-phenylethyl]trimethyl-silylamine or bis[(R)-1-phenylethyl]amine to α,β-unsaturated esters provides an efficient methodology for the asymmetric synthesis of β-amino acids. Trapping of the intermediate enolate with D2O yields α-deuterated β-amino acids with excellent stereoselectivity.
Stereoselective Synthesis of β-Homothreonine and 3-Amino Substituted Carbohydrates
M. Körner, M. Findeisen, N. Sewald,
β-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 γ-alkoxy enoates. The product configuration can either be controlled by the reagent irrespective of the substrate stereochemistry or is complementary to other procedures.