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Enantioselective Phase-Transfer Catalyzed α-Sulfanylation of Isoxazolidin-5-ones: An Entry to β 2,2 -Amino Acid Derivatives

Abstract : An unprecedented enantioselective α‐functionalization of C4‐substituted N‐alkoxycarbonyl isoxazolidin‐5‐ones, readily available platforms from Meldrum's acid derivatives, by N‐sulfanylphthalimide (PhthSR) electrophiles was achieved upon an efficient phase‐transfer catalytic approach, mediated by a commercial N‐spiro quaternary ammonium catalyst. Two catalytic activities of the in situ formed R4N+Phth− species were highlighted, the phtalimidate being involved in the anion metathesis event and likely as a Brønsted base. This sequence offers a straightforward access to α,α‐disubstituted isoxazolidinones, which turned out to be useful precursors of α‐sulfanyl‐β2,2‐amino acid derivatives.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-01830257
Contributor : Jocelyne Levillain <>
Submitted on : Wednesday, July 4, 2018 - 5:58:52 PM
Last modification on : Thursday, July 2, 2020 - 3:19:23 AM

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Timothée Cadart, Clément Berthonneau, Vincent Levacher, Stéphane Perrio, Jean-François Brière. Enantioselective Phase-Transfer Catalyzed α-Sulfanylation of Isoxazolidin-5-ones: An Entry to β 2,2 -Amino Acid Derivatives. Chemistry - A European Journal, Wiley-VCH Verlag, 2016, 22 (43), pp.15261-15264. ⟨10.1002/chem.201603910⟩. ⟨hal-01830257⟩

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