Please use this identifier to cite or link to this item: https://hdl.handle.net/11147/14242
Title: Iron-Promoted 1,5-Substitution Reaction of Endocyclic Enyne Oxiranes with MeMgBr: A Stereoselective Method for the Synthesis of Exocyclic 2,4,5-Trienol Derivatives
Authors: Kuş, Melih
Omur, Cenk
Karaca, Sila
Artok, Levent
Keywords: enyne oxiranes
vinylallenes
2,4,5-trienols
iron-catalyzed
1,5-substitution
enantiopure allenes
Palladium-Catalyzed Alkoxycarbonylation
Electrocyclic Ring-Closure
Enantioselective Synthesis
Asymmetric Epoxidation
Grignard-Reagents
Diastereoselective Method
Propargyl Carboxylates
Conjugate Addition
Coupling Reactions
Hydrogen Shifts
Publisher: MDPI
Abstract: The iron-promoted 1,5-substitution reaction of endocyclic oxiranes with MeMgBr yields exocyclic 2,4,5-trienols with high diastereomeric ratios of up to 100:0. However, for the method's success, the oxirane ring must have a trans-configuration. The reactions exhibit strong stereoselectivity concerning the methylation mode and the configuration of the resulting exocyclic double bond. Enantiomerically pure enyne oxiranes can be synthesized through Sharpless asymmetric dihydroxylation and subsequent manipulations. With these reagents, it has been possible to produce exocyclic 2,4,5-trienols in enantiopure forms. Importantly, this process maintains chirality without degradation during the center-to-axis transfer of chirality.
URI: https://doi.org/10.3390/chemistry5040173
https://hdl.handle.net/11147/14242
ISSN: 2624-8549
Appears in Collections:Scopus İndeksli Yayınlar Koleksiyonu / Scopus Indexed Publications Collection
WoS İndeksli Yayınlar Koleksiyonu / WoS Indexed Publications Collection

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