Enantioselective synthesis of both enantiomers of 2-amino-2-(2-furyl) ethan-1-ol as a flexible building block for the preparation of serine and azasugars

…, Ö Sesenoglu, H Aksoy-Cam, H Kaya, K Aydogan

Index: Demir, Ayhan S.; Sesenoglu, Oezge; Aksoy-Cam, Hilal; Kaya, Handan; Aydogan, Kenan Tetrahedron Asymmetry, 2003 , vol. 14, # 10 p. 1335 - 1340

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Citation Number: 23

Abstract

The selective conversion of 1-(2-furyl)-2-hydroxyethan-1-one and ethyl 2-(2-furyl)-2-oxo acetate into (E)-and (Z)-oximes and oxime ethers followed by oxazaborolidine-catalyzed enantioselective reduction using different amino alcohols furnished both enantiomers of the important chiral building block 2-amino-2-(2-furyl) ethan-1-ol with an ee of up to 96%.