Universität zu Köln

Ratsch, Friederike and Schmalz, Hans-Guenther ORCID: 0000-0003-0489-1827 (2018). An Atom-Economic and Stereospecific Access to Trisubstituted Olefins through Enyne Cross Metathesis Followed by 1,4-Hydrogenation. Synlett, 29 (6). S. 785 - 793. STUTTGART: GEORG THIEME VERLAG KG. ISSN 1437-2096

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Abstract

The combination of intermolecular enyne cross metathesis and subsequent 1,4-hydrogenation opens a stereocontrolled and atom-economic access to trisubstituted olefins. By investigating different combinations of functionalized alkyne and alkene substrates, we found that the outcome (yield, E/Z ratio) of the Grubbs II-catalyzed enyne cross-metathesis step depends on the substrate's structure, the amount of the alkene (used in excess), and the (optional) presence of ethylene. In any case, the 1,4-hydrogenation, catalyzed by 1,2-di-methoxybenzene-Cr(CO) 3, proceeds stereospecifically to yield exclusively the E-products from both the E-and Z-1,3-diene intermediates obtained by metathesis. A rather broad scope and functional group compatibility of the method is demonstrated by means of 15 examples.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Ratsch, Friederike UNSPECIFIED UNSPECIFIED UNSPECIFIED Schmalz, Hans-Guenther UNSPECIFIED orcid.org/0000-0003-0489-1827 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-190243
DOI:	10.1055/s-0036-1591528
Journal or Publication Title:	Synlett
Volume:	29
Number:	6
Page Range:	S. 785 - 793
Date:	2018
Publisher:	GEORG THIEME VERLAG KG
Place of Publication:	STUTTGART
ISSN:	1437-2096
Language:	English
Faculty:	Unspecified
Divisions:	Unspecified
Subjects:	no entry
Uncontrolled Keywords:	Keywords Language CARBENE COMPLEXES; ORGANIC-SYNTHESIS; GRUBBS RUTHENIUM; CATALYSTS; 1,4-CIS-HYDROGENATION; MECHANISM; ROUTE Multiple languages Chemistry, Organic Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/19024