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Palladium-catalyzed stereoselective domino arylation–acylation: an entry to chiral tetrahydrofluorenone scaffolds

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Abstract

A palladium-catalyzed domino arylation-cyclization of biocatalytically derived cyclic 1,3-dienes is demonstrated. The reaction introduces a high degree of structural complexity in a single step, giving access to tricyclic tetrahydrofluorenones with full regio- and stereoselectivity. The transformation proceeds through a novel acylation-terminated Heck-type sequence, and quantum chemical calculations indicate that C–H activation is involved in the terminating acylation step.

Graphical abstract: Palladium-catalyzed stereoselective domino arylation–acylation: an entry to chiral tetrahydrofluorenone scaffolds

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Article information


Submitted
23 Apr 2021
Accepted
02 Jun 2021
First published
02 Jun 2021

This article is Open Access

Chem. Commun., 2021, Advance Article
Article type
Communication

Palladium-catalyzed stereoselective domino arylation–acylation: an entry to chiral tetrahydrofluorenone scaffolds

P. Dunås, A. J. Paterson, G. Kociok-Köhn, M. Rahm, S. E. Lewis and N. Kann, Chem. Commun., 2021, Advance Article , DOI: 10.1039/D1CC02160E

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