Enantioselective Phase-Transfer Catalyzed α-Sulfanylation of Isoxazolidin-5-ones: An Entry to β 2,2 -Amino Acid Derivatives - Normandie Université Access content directly
Journal Articles Chemistry - A European Journal Year : 2016

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.

Dates and versions

hal-01830257 , version 1 (04-07-2018)

Identifiers

Cite

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, 2016, 22 (43), pp.15261-15264. ⟨10.1002/chem.201603910⟩. ⟨hal-01830257⟩
33 View
0 Download

Altmetric

Share

Gmail Facebook X LinkedIn More