Universität zu Köln

Lansing, Markus, Engler, Hauke ORCID: 0000-0003-1538-5444, Leuther, Tobias M., Neudoerfl, Joerg-M. and Berkessel, Albrecht ORCID: 0000-0003-0470-7428 (2016). Titanium cis-1,2-Diaminocyclohexane Salalen Catalysts of Outstanding Activity and Enantioselectivity for the Asymmetric Epoxidation of Nonconjugated Terminal Olefins with Hydrogen Peroxide. ChemCatChem, 8 (24). S. 3706 - 3710. WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1867-3899

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Abstract

We report a new and readily accessible class of titanium salalen complexes derived from cis-1,2-diaminocyclohexane (cis-DACH) and fluorinated salicylic aldehyde derivatives. With aqueous hydrogen peroxide as the oxidant, these complexes catalyze the epoxidation of terminal, nonconjugated olefins in high yields with high enantioselectivities. We furthermore discovered that the addition of certain acidic or basic co-catalysts significantly accelerated the epoxidation. For example, in the presence of 1 mol% Ti catalyst and 1 mol% pentafluorobenzoic acid, 1-octene epoxidation (95% ee) was completed at room temperature within 8 h. The catalytic process was compatible with many functional groups (e. ., ethers, esters, halides, nitriles, and nitro groups), whereas free hydroxy groups appeared to slow down the reaction to some extent. Catalyst recycling was possible.

Item Type:	Journal Article
Creators:	Creators Email ORCID ORCID Put Code Lansing, Markus UNSPECIFIED UNSPECIFIED UNSPECIFIED Engler, Hauke UNSPECIFIED orcid.org/0000-0003-1538-5444 UNSPECIFIED Leuther, Tobias M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Neudoerfl, Joerg-M. UNSPECIFIED UNSPECIFIED UNSPECIFIED Berkessel, Albrecht UNSPECIFIED orcid.org/0000-0003-0470-7428 UNSPECIFIED
URN:	urn:nbn:de:hbz:38-252373
DOI:	10.1002/cctc.201601154
Journal or Publication Title:	ChemCatChem
Volume:	8
Number:	24
Page Range:	S. 3706 - 3710
Date:	2016
Publisher:	WILEY-V C H VERLAG GMBH
Place of Publication:	WEINHEIM
ISSN:	1867-3899
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 Chemistry, Physical Multiple languages
Refereed:	Yes
URI:	http://kups.ub.uni-koeln.de/id/eprint/25237