Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC‐Catalyzed Kinetic Resolution
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, 3657-3661. https://doi.org/10.1002/ejoc.202100491
Published inEuropean Journal of Organic Chemistry
DisciplineEpäorgaaninen ja analyyttinen kemiaEpäorgaaninen kemiaInorganic and Analytical ChemistryInorganic Chemistry
© 2021 The Authors. European Journal of Organic Chemistry published by Wiley-VCH GmbH
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.
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Additional information about fundingFunding 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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