An asymmetric synthesis of both enantiomers of 2,2,2-trifluoro-1-furan-2-yl-ethylamine and 3,3,3-trifluoroalanine from 2,2,2-trifluoro-1-furan-2-yl-ethanone

The selective conversion of 2,2,2-trifluoro-1-furan-2-yl-ethanone into ( E)- and ( Z)-oximes and oxime ethers and subsequent oxazaborolidine-catalyzed enantioselective reduction using different amino alcohols furnished both enantiomers of the important chiral building block 2,2,2-trifluoro-1-furan-2...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 2001-09, Vol.12 (16), p.2309-2313
Main Authors: Demir, Ayhan S., Sesenoglu, Özge, Gerçek-Arkin, Zuhal
Format: Article
Language:English
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Summary:The selective conversion of 2,2,2-trifluoro-1-furan-2-yl-ethanone into ( E)- and ( Z)-oximes and oxime ethers and subsequent oxazaborolidine-catalyzed enantioselective reduction using different amino alcohols furnished both enantiomers of the important chiral building block 2,2,2-trifluoro-1-furan-2-yl-ethylamine with e.e. of up to 88%. Oxidation of the furan ring afforded both enantiomers of 3,3,3-trifluoroalanine in 91–93% yields. Graphic
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(01)00410-4