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Construction of Isoxazolidin-5-ones with a Tetrasubstituted Carbon Center: Enantioselective Conjugate Addition Mediated by Phase-Transfer Catalysis

Abstract : An efficient enantioselective Michael reaction of readily available α‐substituted N‐Boc isoxazolidin‐5‐ones is described under phase transfer conditions with up to 95:5 er. The organocatalytic process is promoted by a low catalytic loading of a commercially available N‐spiro quaternary ammonium salt. This sequence opens an entry to chiral heterocyclic platforms displaying a β‐amino carbonyl motif with an α‐all‐carbon quaternary stereogenic center. The methodology was also successfully extended to the asymmetric amination reaction using an azodicarboxylate electrophile.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-01830254
Contributor : Jocelyne Levillain <>
Submitted on : Wednesday, July 4, 2018 - 5:56:57 PM
Last modification on : Wednesday, July 1, 2020 - 12:44:30 PM

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Timothée Cadart, Vincent Levacher, Stéphane Perrio, Jean-François Brière. Construction of Isoxazolidin-5-ones with a Tetrasubstituted Carbon Center: Enantioselective Conjugate Addition Mediated by Phase-Transfer Catalysis. Advanced Synthesis and Catalysis, Wiley-VCH Verlag, 2018, 360 (7), pp.1499-1509. ⟨10.1002/adsc.201800009⟩. ⟨hal-01830254⟩

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