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 e nantioselective reduction using different amino alcohols furnished both ena ntiomers of the important chiral building block 2,2,2-trifluoro-1-furan-2-y l-ethylamine with e.e. of up to 88%. Oxidation of the furan ring afforded b oth enantiomers of 3,3,3-trifluoroalanine in 91-93% yields. (C) 2001 Elsevi er Science Ltd. All rights reserved.