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Chiral induction in intramolecular rhodium-catalyzed [2+2+2] cycloadditions of optically active allene-ene/yne-allene substrates
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Allene-yne-allene and allene-ene-allene N-tosyl-linked substrates with two chiral centres in the α-position of the allene moiety were satisfactorily prepared starting both from racemic and chiral propargylic alcohols. The Wilkinson's complex-catalyzed [2+2+2] cycloaddition reaction of these substrates was evaluated. In the case of enantiomerically pure bisallenes, perfect stereoselectivity was observed, giving a diastereomerically pure cycloadduct. The chirality of starting bisallene substrates can be completely transferred to the cycloadducts, representing an atom-economical and enantiospecific process for the construction of fused polycycles. However, when reacting an oxygen-linked allene-ene-allene substrate, the stereoselectivity decreased and two diastereoisomers were formed. A detailed characterization study of the resulting cycloadducts allows us to identify the enantioisomer generated in the cycloaddition.
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HARABURDA, Ewelina, FERNÁNDEZ, Martí, GIFREU, Anna, GARCÍA GÓMEZ, Jordi, PARELLA, Teodor, PLA-QUINTANA, Anna, ROGLANS I RIBAS, Anna. Chiral induction in intramolecular rhodium-catalyzed [2+2+2] cycloadditions of optically active allene-ene/yne-allene substrates. _Advanced Synthesis & Catalysis_. 2017. Vol. 359, núm. 3, pàgs. 506-512. [consulta: 24 de gener de 2026]. ISSN: 1615-4150. [Disponible a: https://hdl.handle.net/2445/106924]