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 editorsAxelsson, Anton; Westerlund, Mathias; Zacharias, Savannah C.; Runemark, August; Haukka, Matti; Sundén, Henrik

Journal or seriesEuropean Journal of Organic Chemistry

ISSN1434-193X

eISSN1099-0690

Publication year2021

Publication date06/07/2021

Volume2021

Issue number25

Pages range3657-3661

PublisherWiley

Publication countryGermany

Publication languageEnglish

DOIhttps://doi.org/10.1002/ejoc.202100491

Publication open accessOpenly available

Publication channel open accessPartially 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.


Keywordschemical reactionssynthesischemical synthesis


Contributing organizations


Ministry reportingYes

Reporting Year2021

JUFO rating1


Last updated on 2024-03-04 at 19:47