Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC-Catalyzed Kinetic Resolution
Artikel i vetenskaplig tidskrift, 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
Författare
Anton Axelsson
Chalmers, Kemi och kemiteknik, Kemi och biokemi
Mathias Westerlund
Student vid Chalmers
S. Zacharias
Göteborgs universitet
August Runemark
Chalmers, Kemi och kemiteknik, Kemi och biokemi
Matti Haukka
Jyväskylän Yliopisto
Henrik Sundén
Göteborgs universitet
Chalmers, Kemi och kemiteknik, Kemi och biokemi
European Journal of Organic Chemistry
1434-193X (ISSN) 10990690 (eISSN)
Vol. 2021 25 3657-3661Ämneskategorier
Oorganisk kemi
Biokatalys och enzymteknik
Organisk kemi
DOI
10.1002/ejoc.202100491