Universität zu Köln

Dindaroglu, Mehmet, Dincer, Akyol and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2014). Synthesis of C-2-Symmetric Bisphosphine Ligands from Tartaric Acid, and Their Performance in the Pd-Catalyzed Asymmetric O-Allylation of a Phenol. Eur. J. Org. Chem., 2014 (20). S. 4315 - 4327. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1099-0690

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Abstract

Starting from tartaric acid derived chiral diols or dicarboxylic acid dichlorides with either a 2,2-dimethyl-1,3-dioxolane (Taddol) or a 2,3-dimethoxy-2,3-dimethyl-1,4-dioxane (Tatrol) core structure, and BH3-protected ortho-phosphanyl phenols, a set of fourteen new C-2-symmetric diphosphine ligands was synthesized. In addition, three related ligands were obtained from ortho-diphenylphosphino-anilines. The fully characterized ligands were then tested in the Pd-catalyzed enantioselective O-allylation of 4-methoxyphenol using crotyl methyl carbonate as a reagent. In addition, a pseudo-intramolecular variant of the reaction, using crotyl 4-methoxyphenyl carbonate as a substrate, was studied. The so-called Trost ligand was used as a reference. Although the Trost ligand (3 mol-%) gave up to 84% ee, one of the new ligands showed higher activity (50% ee with 0.075 mol-%).

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Dindaroglu, Mehmet UNSPECIFIED UNSPECIFIED UNSPECIFIED Dincer, Akyol UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-435241
DOI:	10.1002/ejoc.201402326
Journal or Publication Title:	Eur. J. Org. Chem.
Volume:	2014
Number:	20
Page Range:	S. 4315 - 4327
Date:	2014
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 PHOSPHINE-PHOSPHITE-LIGANDS; ALLYLIC ALKYLATIONS; GRIGNARD-REAGENTS; 1,4-ADDITION; AUXILIARIES; VITAMIN Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/43524