1,4-ADDITIONS OF AMINES TO 5-METHOXYFURAN-2(5H)-ONE; AN EFFICIENT SYNTHESIS OF AMINO

Abstract: The 1,4-addition of various primary and secondary amines to 5-methoxyfuran-2(5H)-one in N,N-dimethylformamide or methylene chloride at room temperature affords quantitatively β-amino lactones 1a-g. The latter compounds are conveniently reduced to amino diols in high yields. Under similar conditions l-(α)-methylbenzylamine gave optically active amino diols. Amino alcohols have found widespread application as intermediates in organic synthesis. The 1,2-and 1,3-amino alcohol structural entity is common to several classes of biologically active compounds.1 Furthermore, the synthesis of various ligands for transition metal catalysts is based upon amino alcohols.2 A number of routes to these compounds have been developed starting from, e.g. epoxides, cyanohydrines or amino acids.3 In recent years amino acids have also served as chiral building blocks for various optically active amino alcohols and derivatives which have found uses as chiral ligands or chiral auxiliaries in asymmetric syntheses.4 With the aim of developing new and flexible routes to amino alcohols and amino diols we hav