Palladium Catalyzed Stereoselective Arylation of Biocatalytically Derived Cyclic 1,3-Dienes: Chirality Transfer via a Heck-Type Mechanism
Artikel i vetenskaplig tidskrift, 2020

Microbial arene oxidation of benzoic acid with Ralstonia eutropha B9 provides a chiral highly functionalized cyclohexadiene, suitable for further structural diversification. Subjecting this scaffold to a Pd-catalyzed Heck reaction effects a regio- and stereoselective arylation of the cyclohexadiene ring, with 1,3-chirality transfer of stereogenic information installed in the microbial arene oxidation. Quantum chemical calculations explain the selectivity both by a kinetic preference for the observed arylation position and by reversible carbopalladation in competing positions. Further product transformation allowed the formation of a tricyclic ketone possessing four stereogenic centers. This demonstrates the capability of the method to introduce stereochemical complexity from planar nonchiral benzoic acid in just a few steps.


Andrew Paterson

Chalmers, Kemi och kemiteknik, Kemi och biokemi

Petter Dunås

Chalmers, Kemi och kemiteknik, Kemi och biokemi

Martin Rahm

Chalmers, Kemi och kemiteknik, Kemi och biokemi

Per-Ola Norrby

AstraZeneca AB

G. Kociok-Köhn

University of Bath

Simon E. Lewis

University of Bath

Nina Kann

Chalmers, Kemi och kemiteknik, Kemi och biokemi

Organic Letters

1523-7060 (ISSN) 1523-7052 (eISSN)

Vol. 22 6 2464-2469


Biokemi och molekylärbiologi

Biokatalys och enzymteknik

Organisk kemi



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