Grauer, Andreas and Späth, Andreas and Ma, Dawai and König, Burkhard (2009) Metal-catalyzed derivatization of C-tetrasubstituted amino acids and their use in the synthesis of cyclic peptides. Chemistry - An Asian Journal 4 (7), pp. 1134-1140.
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C-tetrasubstituted amino acids are important building blocks in the design and preparation of novel peptidomimetics. We report on the functionalization of the C-tetrasubstituted THF amino acid rac-5 by copper(I) catalyzed N-arylation reactions. The aryl bromide substituent of rac-5 is replaced by a variety of aliphatic and aromatic amines. Intramolecular N-arylation yielded only small amounts of a cyclic tripeptide 2, whereas cyclic tripeptide ethers 4 and 50 were obtained in an enantiomerically pure form from a palladium(0)-catalyzed intramolecular O-arylation.
|Institutions:||Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König|
|Keywords:||amino acids; cyclization; homogeneous catalysis; peptides; peptidomimetics|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Created at the University of Regensburg:||Yes|
|Deposited On:||14 Jul 2009 10:19|
|Last Modified:||24 Oct 2012 10:33|