Berkessel, Albrecht 
ORCID: 0000-0003-0470-7428
(2019).
Titanium Salalen Catalysts for the Asymmetric Epoxidation of Terminal (and Other Unactivated) Olefins with Hydrogen Peroxide.
Aldrichimica Acta, 52 (1).
S. 23 - 32.
MILWAUKEE:
ALDRICH CHEMICAL CO INC.
ISSN 0002-5100
Abstract
The epoxidation of terminal, unconjugated olefins with high stereoselectivity has been a long-standing problem in asymmetric catalysis. In this review, we describe the development of titanium salalen catalysts which provide a practical solution to this problem. This type of epoxidation catalyst employs aqueous hydrogen peroxide as terminal oxidant, which makes this method even more attractive from a preparative point of view. The best salalen ligands for this purpose are derived from cis-DACH as the chiral building block, and the one such ligand incorporating two 3-(pentafluorophenyl)salicylic aldehyde moieties (9c, Berkessel ligand) currently affords the most effective and selective titanium catalyst in this regard. In addition to several examples of the recent use of titanium salalen epoxidation in natural product synthesis, practical hints for catalyst preparation and application are presented. Structural and mechanistic aspects of titanium salalens are briefly addressed as well.
| Item Type: | Journal Article | ||||||||
| Creators: |
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| URN: | urn:nbn:de:hbz:38-139086 | ||||||||
| Journal or Publication Title: | Aldrichimica Acta | ||||||||
| Volume: | 52 | ||||||||
| Number: | 1 | ||||||||
| Page Range: | S. 23 - 32 | ||||||||
| Date: | 2019 | ||||||||
| Publisher: | ALDRICH CHEMICAL CO INC | ||||||||
| Place of Publication: | MILWAUKEE | ||||||||
| ISSN: | 0002-5100 | ||||||||
| 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: |
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| Refereed: | Yes | ||||||||
| URI: | http://kups.ub.uni-koeln.de/id/eprint/13908 |
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