The synthesis of diastereo- and enantiomerically pure β-aminocyclopropanecarboxylic acids

被引:65
作者
Beumer, R
Bubert, C
Cabrele, C
Vielhauer, O
Pietzsch, M
Reiser, O
机构
[1] Univ Stuttgart, Dept Biochem Engn, D-70569 Stuttgart, Germany
[2] Univ Regensburg, Dept Organ Chem, D-93053 Regensburg, Germany
关键词
D O I
10.1021/jo005541l
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of diastereo- and enantiomerically pure beta -aminocyclopropanecarboxylic acids (beta -ACCs) is described. Starting from pyrrole, (rac)-4 is readily obtained, which was kinetically resolved by enzymatic hydrolysis. Subsequent oxidation of (-)-4 and deformylation gives rise to:the cis-beta -ACC derivative (ent)-9, while (+)-10 was converted to the trans-beta -ACC derivative 8. Both 8 and (ent)-9 and their benzyl esters 13 and is, being conformationally restricted beta -alanine or gamma -aminobutyric acid (GABA) derivatives, represent useful building blocks for peptides containing unnatural amino acids.
引用
收藏
页码:8960 / 8969
页数:10
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