Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 57, Issue 5, Pages 1246-1250Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201710694
Keywords
cycloaddition; enantioselectivity; fulvenes; organocatalysis; reaction mechanisms
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Funding
- Carlsberg Foundation Semper Ardens
- Aarhus University
- DNRF
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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 C-2-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.
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