Organocatalytic Enantioselective Higher-Order Cycloadditions of In Situ Generated Amino Isobenzofulvenes

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The [8+2] cycloaddition of indene-2-carbaldehydes and nitro olefins is described to provide benzonorbornene scaffolds in a highly peri-, diastereo-, and enantioselective fashion in the presence of a C2-symmetric aminocatalyst. This reaction, which proceeds through a transient semi-aromatic amino isobenzofulvene, represents the first example of catalytic formation and transformation of these species. Quantum chemical calculations suggest a kinetically controlled stepwise mechanism where the stereochemistry is determined in the first bond-forming event. Beyond the useful [8+2] cycloadducts, [10+4] cycloadducts have been identified in silico as potential off-pathway intermediates.

Original languageEnglish
JournalAngewandte Chemie - International Edition
Pages (from-to)1246-1250
Number of pages5
Publication statusPublished - 26 Jan 2018

    Research areas

  • cycloaddition, enantioselectivity, fulvenes, organocatalysis, reaction mechanisms

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