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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

✍ Scribed by Ayhan S. Demir; Özge Sesenoglu; Hilal Aksoy-Cam; Handan Kaya; Kenan Aydogan

Publisher: Elsevier Science
Year: 2003
Tongue: English
Weight: 270 KB
Volume: 14
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(03)00158-7

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✦ Synopsis

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%.

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