Chiral Induction in Intramolecular Rhodium-Catalyzed [2+2+2] Cycloadditions of Optically Active Allene–ene/yne–allene Substrates

Ewelina Haraburda, Martí Fernández, Anna Gifreu, Jordi Garcia, Teodor Parella, Anna Pla-Quintana, Anna Roglans

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    7 Citations (Scopus)

    Abstract

    © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim 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, high 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 allowed us to identify the enantioisomer generated in the cycloaddition. (Figure presented.).
    Original languageEnglish
    Pages (from-to)506-512
    JournalAdvanced Synthesis and Catalysis
    Volume359
    Issue number3
    DOIs
    Publication statusPublished - 1 Jan 2017

    Keywords

    • Allenes
    • Chiral induction
    • Cycloaddition
    • Polycycle
    • Rhodium

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