Beumer, Raphael and Bubert, Christian and Cabrele, Chiara and Vielhauer, Oliver and Pietzsch, Markus and Reiser, Oliver (2000) The Synthesis of Diastereo- and Enantiomerically Pure β-Aminocyclopropane Carboxylic Acids. Journal of Organic Chemistry 65 (26), pp. 8960-8969.
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Other URL: http://dx.doi.org/10.102/jo005541l
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.
|Date:||29 December 2000|
|Institutions:|| Chemistry and Pharmacy > Institut für Organische Chemie > Arbeitskreis Dr. Chiara Cabrele|
Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Oliver Reiser
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Unknown|
|Owner:||Helge Knüttel (ADMIN)|
|Deposited On:||01 Sep 2006|
|Last Modified:||05 Aug 2009 13:22|