Universität zu Köln

Albat, Dominik, Neudoerfl, Joerg-Martin and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2021). A General Stereocontrolled Synthesis of Opines through Asymmetric Pd-Catalyzed N-Allylation of Amino Acid Esters. Eur. J. Org. Chem., 2021 (14). S. 2099 - 2103. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1099-0690

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Abstract

A stereo-divergent synthesis of natural and unnatural opines in stereochemically pure form is based on the direct palladium-catalyzed N-allylation of alpha-amino acid esters (up to 97 % ee or 99 : 1 d.r.) using methyl (E)-2-penten-4-yl carbonate in the presence of only 1 mol% of a catalyst, prepared in-situ from the C-2-symmetric diphosphine iPr-MediPhos and [Pd(allyl)Cl](2). Selected target compounds (incl. a derivative of the drug enalapril) were efficiently obtained from the N-allylated intermediates by oxidative cleavage (ozonolysis) of the allylic C=C bond under temporary N-Boc-protection.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Albat, Dominik UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-Martin UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-561432
DOI:	10.1002/ejoc.202100259
Journal or Publication Title:	Eur. J. Org. Chem.
Volume:	2021
Number:	14
Page Range:	S. 2099 - 2103
Date:	2021
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1099-0690
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language ALLYLIC AMINATION; BUILDING-BLOCKS; DEHYDROGENASE; METALLOPHORE; ALKYLATIONS; LEAD Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/56143