Universität zu Köln

Albat, Dominik, Koecher, Alicia, Witt, Julia and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2022). On the Asymmetric Iridium-Catalyzed N-Allylation of Amino Acid Esters: Improved Selectivities through Structural Variation of the Chiral Phosphoramidite Ligand. Eur. J. Org. Chem., 2022 (12). WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1099-0690

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Abstract

The investigation of the iridium-catalyzed asymmetric N-allylation of tert-butyl glycinate using a branched racemic 1-vinyl-alkyl methyl carbonate revealed severe limitations of existing protocols. By screening a set of 24 BINOL-derived chiral phosphoramidites a new superior ligand (L24*) was identified which afforded the amination product with high enantioselectivity (>= 9 5 % ee) under optimized conditions. This ligand also allowed the N-allylation of other amino acid tert-butyl esters (derived from alanine, phenylalanine, or proline) with out-standing levels of diastereocontrol (d.r. 99:1) and negligible matched/mismatched differences.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Albat, Dominik UNSPECIFIED UNSPECIFIED UNSPECIFIED Koecher, Alicia UNSPECIFIED UNSPECIFIED UNSPECIFIED Witt, Julia UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-657283
DOI:	10.1002/ejoc.202200188
Journal or Publication Title:	Eur. J. Org. Chem.
Volume:	2022
Number:	12
Date:	2022
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 ENANTIOSELECTIVE ALLYLIC AMINATION; PALLADIUM; SUBSTITUTION; COMPLEXES; DESIGN Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/65728