Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC-Catalyzed Kinetic Resolution
Journal article, 2021

An oxidative NHC-catalyzed kinetic resolution (KR) of racemic mixtures is presented. The developed reaction furnishes tricyclic dihydropyranones with three contiguous stereocenters in excellent dia- and enantioselectivity, with good-to-moderate yields. Mechanistic studies indicate that the rate-determining step of the reaction is the formation of the Breslow intermediate, while the selectivity determining step occurs later in the mechanism. The presented methodology enables rapid synthesis of complex structures in a single step.

Structurally divergent resolution

NHC

Organocatalysis

Oxidative NHC

Author

Anton Axelsson

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry

Mathias Westerlund

Student at Chalmers

S. Zacharias

University of Gothenburg

August Runemark

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

Matti Haukka

University of Jyväskylä

Henrik Sundén

University of Gothenburg

Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry

European Journal of Organic Chemistry

1434-193X (ISSN)

Vol. 2021 25 3657-3661

Subject Categories

Inorganic Chemistry

Biocatalysis and Enzyme Technology

Organic Chemistry

DOI

10.1002/ejoc.202100491

More information

Latest update

7/29/2021