Abstract
The synthesis of diastereo- and enantiomerically pure -aminocyclopropanecarboxylic acids (-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--ACC derivative (ent)-9, while (+)-10 was converted to the trans--ACC derivative 8. Both 8 and (ent)-9 and ...
Abstract
The synthesis of diastereo- and enantiomerically pure -aminocyclopropanecarboxylic acids (-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--ACC derivative (ent)-9, while (+)-10 was converted to the trans--ACC derivative 8. Both 8 and (ent)-9 and their benzyl esters 13 and 16, being conformationally restricted -alanine or -aminobutyric acid (GABA) derivatives, represent useful building blocks for peptides containing unnatural amino acids.
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