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Synthesis of Hexahydrocyclopenta[c]furans by an Intramolecular Iron-Catalyzed Ring Expansion Reaction

โœ Scribed by Gerhard Hilt; Patrick Bolze; Maja Heitbaum; Katrin Hasse; Klaus Harms; Werner Massa

Publisher
John Wiley and Sons
Year
2007
Tongue
English
Weight
248 KB
Volume
349
Category
Article
ISSN
1615-4150

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โœฆ Synopsis

Abstract

The intramolecular ironโ€catalyzed ring expansion reaction of epoxyalkenes was investigated with a preformed iron(salen) [Fe(Salen)] complex. The formal insertion of the alkene into the epoxide generated hexahydrocyclopenta[c]furan derivatives in moderate to good yields and diastereoselectivities depending on other functional groups present in the starting materials. In addition, oxygenโ€tethered epoxyalkenes were used for the synthesis of lignan isomers. The scope and limitations of the Fe(Salen)โ€catalyzed process of the reaction are discussed.

๐Ÿ“œ SIMILAR VOLUMES

An Improved Catalyst System for the Iron
An Improved Catalyst System for the Iron-Catalyzed Intermolecular Ring-Expansion Reactions of Epoxides
โœ Gerhard Hilt; Patrick Bolze; Klaus Harms ๐Ÿ“‚ Article ๐Ÿ“… 2007 ๐Ÿ› John Wiley and Sons ๐ŸŒ English โš– 359 KB ๐Ÿ‘ 1 views

## Abstract A considerable improvement is reported in the ironโ€catalyzed ringโ€expansion reactions of epoxides generating tetrahydrofuran derivatives by formal insertion of an alkene. Optimization of the catalyst system revealed that a preformed [Fe(salen)] complex minimizes the formation of polymer