Universität zu Köln

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:	Creators Email ORCID ORCID Put Code Dohmen, Stephan UNSPECIFIED UNSPECIFIED UNSPECIFIED Reiher, Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED Albat, Dominik UNSPECIFIED UNSPECIFIED UNSPECIFIED Akyol, Sema UNSPECIFIED UNSPECIFIED UNSPECIFIED Barone, Matthias UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED Kuehne, Ronald UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED
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:	Faculty of Mathematics and Natural Sciences
Divisions:	Faculty of Mathematics and Natural Sciences > Department of Chemistry > Institute of Organic Chemistry
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language ENANTIOSELECTIVE ALLYLIC AMINATION; STEREOSELECTIVE-SYNTHESIS; BUILDING-BLOCKS; LIGAND DESIGN; PALLADIUM; SUBSTITUTION; NUCLEOPHILES; ALKYLATIONS; INDUCTION; PHOSPHINE Multiple languages Chemistry, Multidisciplinary Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/34466