A1 Journal article (refereed)
Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC‐Catalyzed Kinetic Resolution (2021)

Axelsson, A., Westerlund, M., Zacharias, S. C., Runemark, A., Haukka, M., & Sundén, H. (2021). Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC‐Catalyzed Kinetic Resolution. European Journal of Organic Chemistry, 2021(25), 3657-3661. https://doi.org/10.1002/ejoc.202100491

JYU authors or editors

Publication details

All authors or editors: Axelsson, Anton; Westerlund, Mathias; Zacharias, Savannah C.; Runemark, August; Haukka, Matti; Sundén, Henrik

Journal or series: European Journal of Organic Chemistry

ISSN: 1434-193X

eISSN: 1099-0690

Publication year: 2021

Publication date: 06/07/2021

Volume: 2021

Issue number: 25

Pages range: 3657-3661

Publisher: Wiley

Publication country: Germany

Publication language: English

DOI: https://doi.org/10.1002/ejoc.202100491

Publication open access: Openly available

Publication channel open access: Partially open access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/77054

Abstract

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.

Keywords: chemical reactions; synthesis; chemical synthesis

Contributing organizations

Ministry reporting: Yes

Reporting Year: 2021

JUFO rating: 1