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The cascade rearrangement of chiral enediynes 1c-e, involving successively 1,3-proton shift, Saito-Myers cyclization, 1,5-hydrogen atom transfer, and intramolecular coupling of the resulting biradical, proceeded at 80 °C to form tri- and tetracyclic heterocycles possessing a quaternary stereogenic center with a very high level of memory of chirality.


Malek Nechab, Damien Campolo, Julien Maury, Patricia Perfetti, Nicolas Vanthuyne, Didier Siri, Michèle P Bertrand. Memory of chirality in cascade rearrangements of enediynes. Journal of the American Chemical Society. 2010 Oct 27;132(42):14742-4

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PMID: 20879786

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