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

Demir A., Sesenoglu O., Aksoy-Cam H., Kaya H., Aydogan K.

TETRAHEDRON-ASYMMETRY, vol.14, no.10, pp.1335-1340, 2003 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 14 Issue: 10
  • Publication Date: 2003
  • Doi Number: 10.1016/s0957-4166(03)00158-7
  • Journal Name: TETRAHEDRON-ASYMMETRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1335-1340
  • Middle East Technical University Affiliated: Yes

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%. (C) 2003 Elsevier Science Ltd. All rights reserved.