The synthesis of diastereo- and enantiomerically pure beta-aminocyclopropanecarboxylic acids.
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 16, being conformationally restricted beta-alanine or gamma-aminobutyric acid (GABA) derivatives, represent useful building blocks for peptides containing unnatural amino acids.
Beumer
R
R
Department of Organic Chemistry, University of Regensburg, Universitätsstr. 31, D-93053 Regensburg, Germany.
Bubert
C
C
Cabrele
C
C
Vielhauer
O
O
Pietzsch
M
M
Reiser
O
O
D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002851:Chromatography, High Pressure Liquid; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D006868:Hydrolysis; D007202:Indicators and Reagents; D007700:Kinetics; D008049:Lipase / Q000737:chemistry; D013237:Stereoisomerism
D002264:Carboxylic Acids; D003521:Cyclopropanes; D007202:Indicators and Reagents; D008049:Lipase