Dohmen, Stephan, Reiher, Martin, Albat, Dominik, Akyol, Sema, Barone, Matthias, Neudoerfl, Joerg-Martin, Kuehne, Ronald and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2020). 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. Chem.-Eur. J., 26 (14). S. 3049 - 3054. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3765

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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 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.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Dohmen, StephanUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Reiher, MartinUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Albat, DominikUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Akyol, SemaUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Barone, MatthiasUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Neudoerfl, Joerg-MartinUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Kuehne, RonaldUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Schmalz, Hans-GuentherUNSPECIFIEDorcid.org/0000-0003-0489-1827UNSPECIFIED
URN: urn:nbn:de:hbz:38-344663
DOI: 10.1002/chem.202000307
Journal or Publication Title: Chem.-Eur. J.
Volume: 26
Number: 14
Page Range: S. 3049 - 3054
Date: 2020
Publisher: WILEY-V C H VERLAG GMBH
Place of Publication: WEINHEIM
ISSN: 1521-3765
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
ENANTIOSELECTIVE ALLYLIC AMINATION; STEREOSELECTIVE-SYNTHESIS; BUILDING-BLOCKS; LIGAND DESIGN; PALLADIUM; SUBSTITUTION; NUCLEOPHILES; ALKYLATIONS; INDUCTION; PHOSPHINEMultiple languages
Chemistry, MultidisciplinaryMultiple languages
URI: http://kups.ub.uni-koeln.de/id/eprint/34466

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