4.5 Article

Unprecedented Asymmetric Epoxidation of Isolated Carbon-Carbon Double Bonds by a Chiral Fluorous Fe(III) Salen Complex: Exploiting Fluorophilic Effect for Catalyst Design

期刊

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2019, 期 13, 页码 2401-2408

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201900146

关键词

Epoxidation; Asymmetric catalysis; Salen complex; Fluorous; Fluorophilic effect

资金

  1. JSPS KAKENHI [JP26450145, JP16H04139, JPMJAC1401]

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The first asymmetric epoxidation of isolated carbon-carbon double bonds by a chiral salen complex using ubiquitous Fe(III) as a center-metal is described. By simultaneously introducing fluorous tags and tert-butyl groups into the ligand of the salen complex, asymmetric epoxidation is achieved. The fluorous tags act as both the electron-withdrawing groups, to improve the catalytic activity for oxidation, and the driving force to form a unique asymmetric stereo environment. Crystallographic analysis of the complex revealed that the catalyst has a distinctive umbrella structure based on intramolecular fluorophilic effect. This is the first example of asymmetric catalytic space construction that exploits fluorous space-interaction of neighboring fluorous tags.

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