Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 14, Pages 3049-3053Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202000307
Keywords
asymmetric catalysis; chiral diphosphine ligands; peptide mimetics; protein interactions; transition-metal catalysis
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Funding
- German Federal Ministry of Education and Research [16GW0187]
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A general and powerful method for the stereo-controlled Pd-catalyzed N-allylation of amino acid esters is reported, as a previously largely unsolved synthetic challenge. Employing a new class of tartaric acid-derived C-2-symmetric chiral diphosphane ligands the developed asymmetric amination protocol allows the conversion of various amino acid esters to the N-allylated products with highest levels of enantio- or diastereoselectivity in a fully catalyst-controlled fashion and predictable configuration. Remarkably, the in situ generated catalysts also exhibit outstanding levels of activity (ligand acceleration). The usefulness of the method was demonstrated in the stereo-divergent synthesis of a set of new conformationally defined dipeptide mimetics, which represent new modular building blocks for the development of peptide-inspired bioactive compounds.
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