Severin, Fabian, Fusi, Giovanni M., Wartmann, Christina ORCID: 0000-0002-3275-8284, Neudoerfl, Jorg-Martin and Berkessel, Albrecht (2022). syn-Selective Epoxidation of Chiral Terminal Allylic Alcohols with a Titanium Salalen Catalyst and Hydrogen Peroxide. Angew. Chem.-Int. Edit., 61 (26). WEINHEIM: WILEY-V C H VERLAG GMBH. ISSN 1521-3773
Full text not available from this repository.Abstract
In the Sharpless asymmetric epoxidation of chiral secondary allylic alcohols, one substrate enantiomer is predominantly converted to the anti-epoxy alcohol. We herein report the first highly syn-selective epoxidation of terminal allylic alcohols using a titanium salalen complex as catalyst, at room temperature, and aqueous hydrogen peroxide as oxidant. With enantiopure terminal allylic alcohols as substrates, the epoxy alcohols were obtained with up to 98 % yield and up to >99 : 1 dr (syn). Catalyst loadings as low as 1 mol % can be applied without eroding the syn-diastereoselectivity. Modification of the allylic alcohol to an ether does not affect the diastereoselectivity either [>99 : 1 dr (syn)]. Inverting the catalyst configuration leads to the anti-product, albeit at lower dr (ca. 20 : 1). The synthetic potential is demonstrated by a short, gram-scale preparation of a tetrahydrofuran building block with three stereocenters, involving two titanium salalen catalyzed epoxidation steps.
Item Type: | Journal Article | ||||||||||||||||||||||||
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URN: | urn:nbn:de:hbz:38-668162 | ||||||||||||||||||||||||
DOI: | 10.1002/anie.202201790 | ||||||||||||||||||||||||
Journal or Publication Title: | Angew. Chem.-Int. Edit. | ||||||||||||||||||||||||
Volume: | 61 | ||||||||||||||||||||||||
Number: | 26 | ||||||||||||||||||||||||
Date: | 2022 | ||||||||||||||||||||||||
Publisher: | WILEY-V C H VERLAG GMBH | ||||||||||||||||||||||||
Place of Publication: | WEINHEIM | ||||||||||||||||||||||||
ISSN: | 1521-3773 | ||||||||||||||||||||||||
Language: | English | ||||||||||||||||||||||||
Faculty: | Unspecified | ||||||||||||||||||||||||
Divisions: | Unspecified | ||||||||||||||||||||||||
Subjects: | no entry | ||||||||||||||||||||||||
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URI: | http://kups.ub.uni-koeln.de/id/eprint/66816 |
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