Issue 91, 2018

Intramolecular cycloaddition/rearrangement cascade from gold(iii)-catalysed reactions of propargyl aryldiazoesters with cinnamyl imines

Abstract

Conjugated cycloheptene-1,4-dione-enamines are cycloaddition products from a surprising rearrangement in a Au(III)-catalysed reaction between propargyl aryldiazoacetates and cinnamyl imines. This complex transformation occurs through an initial rapid Au(III)-catalysed [4+3]-cycloaddition to form dihydroazepinyl aryldiazoacetates followed by a subsequent uncatalyzed domino transformation that occurs by sequential [3+2]-cycloaddition-/nitrogen extrusion and acyloxy migration/retro-Michael addition/tautomerization.

Graphical abstract: Intramolecular cycloaddition/rearrangement cascade from gold(iii)-catalysed reactions of propargyl aryldiazoesters with cinnamyl imines

Supplementary files

Article information

Article type
Communication
Submitted
02 Oct 2018
Accepted
17 Oct 2018
First published
19 Oct 2018

Chem. Commun., 2018,54, 12828-12831

Author version available

Intramolecular cycloaddition/rearrangement cascade from gold(III)-catalysed reactions of propargyl aryldiazoesters with cinnamyl imines

H. Qiu, H. Arman, W. Hu and M. P. Doyle, Chem. Commun., 2018, 54, 12828 DOI: 10.1039/C8CC07885H

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