Universität zu Köln

Chiha, Slim, Soicke, Arne, Barone, Matthias, Mueller, Matthias, Bruns, Judith, Opitz, Robert, Neudoerfl, Joerg-Martin, Kuehne, Ronald and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2018). Design and Synthesis of Building Blocks for PPII-Helix Secondary-Structure Mimetics: A Stereoselective Entry to 4-Substituted 5-Vinylprolines. Eur. J. Org. Chem., 2018 (4). S. 455 - 461. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1099-0690

Full text not available from this repository.

Abstract

In the course of our studies towards the synthesis of proline-based secondary-structure mimetics, we developed a straightforward methodology for the diastereoselective preparation of 4-alkyl-5-vinyl-substituted proline derivatives. Starting from N-Boc-protected tert-butyl pyroglutamate, -alkylation, lactam reduction and acid-catalyzed methanolysis afforded 4-alkyl-5-methoxyproline derivatives. After BF3-induced formation of an N-acyl-iminium intermediate, the introduction of the 5-vinyl side chain was achieved with high diastereoselectivity by using vinylmagnesium bromide in the presence of AlCl3 or CuBrSMe2 to afford either the cis- or the trans-product, respectively. The utility of the method was demonstrated in the rapid and efficient construction of new diproline mimetics rigidified in a polyproline-type II helix (PPII) conformation.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Chiha, Slim UNSPECIFIED UNSPECIFIED UNSPECIFIED Soicke, Arne UNSPECIFIED UNSPECIFIED UNSPECIFIED Barone, Matthias UNSPECIFIED UNSPECIFIED UNSPECIFIED Mueller, Matthias UNSPECIFIED UNSPECIFIED UNSPECIFIED Bruns, Judith UNSPECIFIED UNSPECIFIED UNSPECIFIED Opitz, Robert 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:38-198374
DOI:	10.1002/ejoc.201701584
Journal or Publication Title:	Eur. J. Org. Chem.
Volume:	2018
Number:	4
Page Range:	S. 455 - 461
Date:	2018
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1099-0690
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 PROTEIN-PROTEIN INTERACTIONS; PROLINE OLIGOPEPTIDES; SMALL MOLECULES; PYROGLUTAMATE; ACID; CONFORMATION; METATHESIS; ALKYLATION; INTERACTS; MECHANISM Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/19837