New Routes to Lipophilic Amino Acids: Synthesis of Alkynyl and Fluoro-Containing Alanine Derivatives

被引：7

作者：

Wuttke, Claudia ^{[1
]}

Ford, Rebecca ^{[1
]}

Lilley, Matthew ^{[1
]}

Grabowska, Urszula ^{[2
]}

Wiktelius, Daniel ^{[2
]}

Jackson, Richard F. W. ^{[1
]}

机构：

[1] Univ Sheffield, Dept Chem, Sheffield S3 7HF, S Yorkshire, England

[2] Medivir AB, S-14122 Huddinge, Sweden

来源：

SYNLETT | 2012年 / 02期

关键词：

amino acids; alkynes; cross-coupling; fluorine; zinc; CROSS-COUPLING REACTIONS; ORGANOZINCATE ANIONS;

D O I：

10.1055/s-0031-1290123

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Branched alpha-amino acids incorporating an alkynyl group have been prepared by copper-catalysed reaction of a serine-derived organozinc reagent with bromoallenes. Substantial improvements to our previously reported Negishi cross-coupling of the serine-derived organozinc reagent with cycloalkenyl triflates are possible using a combination of LiCl and SPhos as ligand. Finally, we report a preliminary example of addition of HF to cycloalkenyl alanine derivatives, leading to the corresponding tertiary fluoride.

引用

页码：243 / 246

页数：4

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