Haraburda, EwelinaFernández, MartíGifreu, AnnaGarcía Gómez, JordiParella, TeodorPla-Quintana, AnnaRoglans i Ribas, Anna2017-02-142018-02-282017-021615-4150https://hdl.handle.net/2445/106924Allene-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.7 p.application/pdfeng(c) Wiley-VCH, 2017RodiCiclització (Química)RhodiumRing formation (Chemistry)info:eu-repo/semantics/article6673892017-02-14info:eu-repo/semantics/openAccess