Catalyst Choice for Highly Enantioselective [3 + 3]-Cycloaddition of Enoldiazocarbonyl Compounds

Kostiantyn Marichev, Frady G. Adly, Alejandra Carranco, Estevan Garcia, Hadi Arman, Michael Doyle

    Research output: Contribution to journalArticlepeer-review

    43 Citations (Scopus)

    Abstract

    Chiral copper(I) catalysts are preferred over chiral dirhodium(II) catalysts for [3 + 3]-cycloaddition reactions of enoldiazocarbonyl compounds with nitrones and acyliminopyridinium ylides, forming chiral oxazines and pyrazines in very high yield and enantioselectivity. Yields and stereoselectivities from reactions of enoldiazoketones are virtually the same as those from the corresponding esters and amides, but products from enoldiazoketones are precursors to chiral 1,3-dicarbonyl derivatives that provide additional opportunities in heterocyclic synthesis through the formation of pyrazoles and isoxazoles.
    Original languageEnglish
    Pages (from-to)10392–10400
    Number of pages9
    JournalACS Catalysis
    Volume8
    Issue number11
    DOIs
    Publication statusPublished - 2 Nov 2018

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