Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis

Joan Guasch, Irene Giménez-Nueno, Ignacio Funes-Ardoiz, Miguel Bernús, M. Isabel Matheu, Feliu Maseras, Sergio Castillón, Yolanda Díaz

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Abstract

© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim Regio- and stereoselective oxyamination of dienes through a tandem rhodium-catalysed aziridination–nucleophilic opening affords racemic oxazolidinone derivatives, which undergo a kinetic resolution acylation process with amidine-based catalysts (ABCs) to achieve s values of up to 117. This protocol was applied to the enantioselective synthesis of sphingosine.
Original languageEnglish
Pages (from-to)4635-4642
JournalChemistry - A European Journal
Volume24
Issue number18
DOIs
Publication statusPublished - 26 Mar 2018

Keywords

  • enantioselectivity
  • kinetic resolution
  • organocatalysis
  • oxyamination
  • synthesis design

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    Guasch, J., Giménez-Nueno, I., Funes-Ardoiz, I., Bernús, M., Matheu, M. I., Maseras, F., Castillón, S., & Díaz, Y. (2018). Enantioselective Synthesis of Aminodiols by Sequential Rhodium-Catalysed Oxyamination/Kinetic Resolution: Expanding the Substrate Scope of Amidine-Based Catalysis. Chemistry - A European Journal, 24(18), 4635-4642. https://doi.org/10.1002/chem.201705670