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
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) 10990690 (eISSN)
Vol. 2021 25 3657-3661Subject Categories
Inorganic Chemistry
Biocatalysis and Enzyme Technology
Organic Chemistry
DOI
10.1002/ejoc.202100491