ASYMMETRIC 1,4-ADDITIONS TO 5-ALKOXY-2(5H)-FURANONES ENANTIOSELECTIVE SYNTHESIS AND ABSOLUTE CONFIGURATION DETERMINATION OF β-AMINO-γ-BUTYROLACTONES AND AMINO DIOLS

Article abstract of DOI:10.1016/S0040-4020(01)89149-3

The synthesis of enantiomerically pure β-amino-γ-butyrolactones via asymmetric conjugate addition of various amines to 5-methyloxy-2(5H)-furanone is described.This route provides access to new multifunctional homochiral building blocks.The absolute configuration of the β-amino-γ-butyrolactones is established by X-ray analysis and 1H NMR correlation.The conjugate addition of amines to 2(5H)-furanone, 5-alkyl-2(5H)-furanones and 5-alkoxy-2(5H)-furanones was studied and an enhanced reactivity was observed in 2(5H)-furanones due to a γ-alkoxy-effect.The synthetic utility of the asymmetric amine addition is illustrated in an efficient route to various optically pure 2-amino-1,4-butanediols.