Palladium-catalyzed stereoselective domino arylation-acylation: an entry to chiral tetrahydrofluorenone scaffolds
Journal article, 2021

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.

Author

Petter Dunås

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Physical Chemistry

Andrew Paterson

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry

Gabriele Kociok-Kohn

University of Bath

Martin Rahm

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry

Simon E. Lewis

University of Bath

Nina Kann

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry, Physical Chemistry

Chemical Communications

1359-7345 (ISSN)

Vol. 57 53 6518-6521

Subject Categories

Biochemistry and Molecular Biology

Structural Biology

Organic Chemistry

DOI

10.1039/d1cc02160e

PubMed

34105551

More information

Latest update

8/17/2021