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Organocopper-Triggered Cyclisation of Conjugated Diene-ynes: Diastereo- and Enantioselective Synthesis of Indenes

Abstract : Organocopper reagents react with readily available chiral conjugated diene-ynes to give indene derivatives bearing two stereogenic centres. The investigation of this original reaction in optically pure series demonstrates that a double transfer of chirality is operating. A stereocontrolled cascade involving S(N)2' followed by carbocupration and conjugate addition reactions accounts for the total recovery of the initial chirality. The scope and limitations of the reaction were investigated. The high diastereofacial discrimination in the cyclisation step allowed the construction of the quaternary stereocentre with excellent dr and ee, with the opposite configuration depending on the E- or Z-configuration of the alkene in the starting material. Post-functionalisation of indenes allowed the synthesis of indanyl derivatives containing four contiguous stereocentres.
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Submitted on : Thursday, December 1, 2016 - 9:33:14 AM
Last modification on : Thursday, August 13, 2020 - 3:35:07 AM

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Tanzeel Arif, Cyril Borie, Aura Tintaru, Jean-Valère Naubron, Nicolas Vanthuyne, et al.. Organocopper-Triggered Cyclisation of Conjugated Diene-ynes: Diastereo- and Enantioselective Synthesis of Indenes. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2015, 357 (16-17), pp.3611 - 3616. ⟨10.1002/adsc.201500556⟩. ⟨hal-01406322⟩

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