Construction of Isoxazolidin-5-ones with a Tetrasubstituted Carbon Center: Enantioselective Conjugate Addition Mediated by Phase-Transfer Catalysis - Normandie Université Access content directly
Journal Articles Advanced Synthesis and Catalysis Year : 2018

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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hal-01830254 , version 1 (04-07-2018)

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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, 2018, 360 (7), pp.1499-1509. ⟨10.1002/adsc.201800009⟩. ⟨hal-01830254⟩
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