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

被引:30
作者
Demir, AS [1 ]
Sesenoglu, Ö [1 ]
Gerçek-Arkin, Z [1 ]
机构
[1] Middle E Tech Univ, Dept Chem, TR-06531 Ankara, Turkey
关键词
D O I
10.1016/S0957-4166(01)00410-4
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
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. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:2309 / 2313
页数:5
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