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.

OriginalsprogEngelsk
TidsskriftAngewandte Chemie - International Edition
Vol/bind57
Nummer5
Sider (fra-til)1246-1250
Antal sider5
ISSN1433-7851
DOI
StatusUdgivet - 26 jan. 2018

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