The synthesis of diastereo- and enantiomerically pure beta-aminocyclopropanecarboxylic acids.

Abstract

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.

Cite this paper

@article{Beumer2000TheSO, title={The synthesis of diastereo- and enantiomerically pure beta-aminocyclopropanecarboxylic acids.}, author={Raphael Beumer and Christian Bubert and Chiara Cabrele and Oliver Vielhauer and M. Pietzsch and Oliver L. Reiser}, journal={The Journal of organic chemistry}, year={2000}, volume={65 26}, pages={8960-9} }