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- W2324559824 abstract "Convenient access to highly enantioenriched substituted quinolizidines has been achieved by chiral dirhodium(II) carboxylate-catalyzed dearomatizing formal [3 + 3]-cycloaddition of isoquinolinium/pyridinium methylides and enol diazoacetates. Coordination of Lewis basic methylides to dirhodium(II) prompts the rearrangement of the enol-carbene that is bound to dirhodium to produce a donor–acceptor cyclopropene. The donor–acceptor cyclopropene is in equilibrium with the dirhodium-bound enol-carbene and undergoes both enantioselective [3 + 3]-cycloaddition from the dirhodium-bound enol-carbene and diastereoselective [3 + 2]-cycloaddition by uncatalyzed reaction of the cyclopropene with isoquinolinium or pyridinium methylides. Increasing the mol % of catalyst loading suppresses the [3 + 2]-cycloaddition pathway." @default.
- W2324559824 created "2016-06-24" @default.
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- W2324559824 date "2013-08-09" @default.
- W2324559824 modified "2023-10-17" @default.
- W2324559824 title "Catalytic Asymmetric Syntheses of Quinolizidines by Dirhodium-Catalyzed Dearomatization of Isoquinolinium/Pyridinium Methylides–The Role of Catalyst and Carbene Source" @default.
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- W2324559824 doi "https://doi.org/10.1021/ja406482q" @default.
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