Pd-Catalyzed Asymmetric N-Allylation of Amino Acid Esters with Exceptional Levels of Catalyst Control: Stereo-Divergent Synthesis of ProM-15 and Related Bicyclic Dipeptide Mimetics.
Chemistry
; 26(14): 3049-3053, 2020 Mar 09.
Article
em En
| MEDLINE
| ID: mdl-31961029
ABSTRACT
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 C2 -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.
Palavras-chave
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Paládio
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Dipeptídeos
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Ésteres
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Aminoácidos
Idioma:
En
Ano de publicação:
2020
Tipo de documento:
Article