Mechanochemical synthesis of unsymmetrical salens for the preparation of Co-salen complexes and their evaluation as catalysts for the synthesis of α-aryloxy alcohols via asymmetric phenolic kinetic resolution of terminal epoxides

In this paper, we report the mechanochemical synthesis of unsymmetrical salens using grinding and ball milling technologies, respectively, both of which were afforded in good yield. The chelating effect of the unsymmetrical salens with zinc, copper, and cobalt was studied and the chiral Co-salen com...

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Bibliographic Details
Published in:Beilstein journal of organic chemistry 2022, Vol.18 (1), p.1416-1423
Main Authors: Zuo, Shengli, Zheng, Shuxiang, Liu, Jianjun, Zuo, Ang
Format: Article
Language:English
Subjects:
Alcohol
Alcohols
Catalysts
Chemistry
chiral co–salen
Chromatography
Column chromatography
Epoxides
hkr
Letter
mechanochemistry
Metals
Nucleophiles
Phenolic compounds
phenolic kr
Phenols
α-aryloxy alcohols
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Summary:In this paper, we report the mechanochemical synthesis of unsymmetrical salens using grinding and ball milling technologies, respectively, both of which were afforded in good yield. The chelating effect of the unsymmetrical salens with zinc, copper, and cobalt was studied and the chiral Co-salen complex was obtained in 98% yield. Hydrolytic kinetic resolution (HKR) of epichlorohydrin with water catalyzed by complex (0.5 mol %) was explored and resulted in 98% ee, suggesting complex could serve as an enantioselective catalyst for the asymmetric ring opening of terminal epoxides by phenols. A library of α-aryloxy alcohols was thereafter synthesized in good yield and high ee using via the phenolic KR of epichlorohydrin.
ISSN:1860-5397
2195-951X
1860-5397
DOI:10.3762/bjoc.18.147