Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC‐Catalyzed Kinetic Resolution
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.
Main Authors
Format
Articles
Research article
Published
2021
Series
Subjects
Publication in research information system
Publisher
Wiley
The permanent address of the publication
https://urn.fi/URN:NBN:fi:jyu-202107084240Use this for linking
Review status
Peer reviewed
ISSN
1434-193X
DOI
https://doi.org/10.1002/ejoc.202100491
Language
English
Published in
European Journal of Organic Chemistry
Citation
- 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
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Additional information about funding
Funding from the Swedish Research Council (VR 2014-04664 and Formas 2016-00484, 2019-00699) is gratefully acknowledged.S.C.Z. thanks Olle Engkvist Stiftelse and Å-forsk Foundation for thepostdoctoral fellowship funding
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