Synthesis of α-trifluoromethyl α-amino acids with aromatic, heteroaromatic and ferrocenyl subunits in the side chain

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作者
K. Burger
L. Hennig
P. Tsouker
J. Spengler
F. Albericio
B. Koksch
机构
[1] University of Leipzig,Department of Organic Chemistry
[2] Institut de Recerca Biomédica de Barcelona,Department of Organic Chemistry
[3] Parc Cientific Barcelona,undefined
[4] FU Berlin,undefined
来源
Amino Acids | 2006年 / 31卷
关键词
Keywords: 5-Fluoro-4-trifluoromethyl-1,3-oxazoles – Nucleophilic heteroaromatic substitution – 1,3-Benzyl group migration versus Claisen rearrangement – α-Trifluoromethylamino acids – Synthetic Tfm-Gly equivalent;
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摘要
5-Benzyloxy-4-trifluoromethyl-1,3-oxazoles, obtained from 5-fluoro-4-trifluoromethyloxazoles and benzyl alcohols, are capable for rearrangements. A 1,3 shift of a benzyl group is the key step of a new general route toward α-trifluoromethyl substituted aromatic and heteroaromatic amino acids, demonstrating that 5-fluoro-4-trifluoromethyl-1,3-oxazole is a synthetic Tfm-Gly equivalent. On reaction with benzpinacol partially fluorinated oxazoles are transformed into bis(trifluoromethyl) substituted 2,5-diamino adipic acid and N-benzoyl-2-benzhydryl-3,3,3-trifluoroalanine.
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