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Paper | Regular issue | Vol 27, No. 5, 1988, pp.1197-1205
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4456
1,4-Additions of Amines to 5-Methoxyfuran-1(5H)-one; an Efficient Synthesis of Amino Diols

Ben L. Feringa* and B. de Lange

*Department of Organic Chemistry, University of Groningen, Nijenborgh 16, 9747 AG Groningen, The Netherlands

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 1-(α)-methylbenzylamine gave optically active amino diols.