Universität zu Köln

Arndt, Marion, Dindaroglu, Mehmet, Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 and Hilt, Gerhard (2012). Ligand Control of the Cobalt-Catalysed 1,4-Hydrovinylation Reaction. Synthesis, 44 (22). S. 3534 - 3543. STUTTGART: GEORG THIEME VERLAG KG. ISSN 1437-210X

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Abstract

The application of cobalt catalysts to the hydrovinylation of unsymmetrical alkenes and 1,3-dienes was investigated using modular phosphine-phosphite ligands to evaluate the influence of the ligands on the regioselectivity of the reaction. While a ligand with a TADDOL subunit (SchmalzPhos) gave the best results for the beta-4 regioisomer, the corresponding BINOL-derived ligand gave predominantly the beta-1 regioisomer. The application of (E)-2-methylpenta-1,3-diene in combination with the (nonracemic) BINOL-derived ligand generated the beta-4 regioisomer in excellent yields and very high regioselectivities for a number of terminal alkenes bearing various functional groups. In one case, the enantiomeric excess of a chiral product, i.e. a 3,5-dimethylhexa-1,4-diene derivative, was determined by chiral RP-HPLC to be 78% ee.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Arndt, Marion UNSPECIFIED UNSPECIFIED UNSPECIFIED Dindaroglu, Mehmet UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED Hilt, Gerhard UNSPECIFIED UNSPECIFIED UNSPECIFIED
URN:	urn:nbn:de:hbz:38-480731
DOI:	10.1055/s-0032-1316796
Journal or Publication Title:	Synthesis
Volume:	44
Number:	22
Page Range:	S. 3534 - 3543
Date:	2012
Publisher:	GEORG THIEME VERLAG KG
Place of Publication:	STUTTGART
ISSN:	1437-210X
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language PHOSPHINE-PHOSPHITE-LIGANDS; BIDENTATE CHELATE LIGANDS; ASYMMETRIC HYDROVINYLATION; ALPHA-OLEFINS; ENANTIOSELECTIVE HYDROVINYLATION; MODULAR APPROACH; DIELS-ALDER; STYRENES; 1,4-ADDITION; DIMERIZATION Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/48073