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, Fysikalisk kemi

Matti Haukka

Jyväskylän Yliopisto

Henrik Sundén

Göteborgs universitet

Chalmers, Kemi och kemiteknik, Kemi och biokemi

European Journal of Organic Chemistry

1434-193X (ISSN)

Vol. 2021 25 3657-3661

Ämneskategorier

Oorganisk kemi

Biokatalys och enzymteknik

Organisk kemi

DOI

10.1002/ejoc.202100491

Mer information

Senast uppdaterat

2021-07-29