Synthesis of α,ω-polyfluorinated α-amino acid derivatives and δ,δ-difluoronorvaline

被引：9
|
作者：
Ulbrich, Dirk [1 ,2 ]
Daniliuc, Constantin G. [1 ]
Haufe, Guenter [1 ,2 ]
机构：
[1] Univ Munster, Inst Organ Chem, Corrensstr 40, D-48149 Munster, Germany
[2] Univ Munster, Cells In Mot Cluster Excellence, Waldeyerstr 15, D-48149 Munster, Germany
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 09期
关键词：
STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; MICHAEL ADDITION; FLUORINE; ENZYMES; BIOCATALYSIS; THIOETHERS; PEPTIDES; PROTEINS; DESIGN;
D O I：
10.1039/c6ob00131a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Intending tosynthesize omega,omega-difluoroalkyl amino acid derivatives by oxidative desulfurization-fluorination reactions of suitable arylthio-2-phthalimido butanoates and pentanoates, in addition to small amounts of the target products, mainly alpha,omega-polyfluorinated amino acid derivatives were formed by additional sulfur-assisted alpha-fluorination. This novel structural motif was verified spectroscopically as well as by X-ray analysis. A plausible mechanism of formation is suggested. Using a different approach, delta, delta-difluoronorvaline hydrochloride was synthesized with at least 36% enantiomeric excess via deoxofluorination of the corresponding aldehyde.
引用
收藏
页码：2755 / 2767
页数：13
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