Conjugate hydrotrifluoromethylation of α,β-unsaturated acyl-oxazolidinones: synthesis of chiral fluorinated amino acids

被引：48

作者：

Erdbrink, Holger ^{[1
]}

Peuser, Ilona ^{[1
]}

Gerling, Ulla I. M. ^{[1
]}

Lentz, Dieter ^{[1
]}

Koksch, Beate ^{[1
]}

Czekelius, Constantin ^{[1
]}

机构：

[1] Free Univ Berlin, Inst Chem & Biochem, D-14195 Berlin, Germany

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2012年 / 10卷 / 43期

关键词：

COPPER-CATALYZED TRIFLUOROMETHYLATION; PERFLUOROALKYL IODIDES; CARBONYL-COMPOUNDS; BETA-SHEET; ALKENES; ORGANOBORANES; COIL; TRIETHYLBORANE; PROPENSITIES; ACTIVATION;

D O I：

10.1039/c2ob26810h

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel conjugate hydrofluoroalkylation of alpha,beta-unsaturated acyl-oxazolidinones is described. Using this method, enantiomerically pure beta-trifluoromethylated amino acids were prepared. Trifluorovaline and trifluoroisoleucine were incorporated into peptides and found to show extremely low alpha-helix propensities.

引用

页码：8583 / 8586

页数：4

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