Enantioselective Phase-Transfer Catalyzed α-Sulfanylation of Isoxazolidin-5-ones: An Entry to β2,2-Amino Acid Derivatives.
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.
Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000, Rouen, France.
Timothée
T
Cadart
Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000, Rouen, France.
Clément
C
Berthonneau
Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000, Rouen, France.
Vincent
V
Levacher
Normandie Univ, ENSICAEN, UNICAEN, CNRS, LCMT, 14000, Caen, France.
Stéphane
S
Perrio
Normandie Univ, INSA Rouen, UNIROUEN, CNRS, COBRA (UMR 6014), 76000, Rouen, France. jean-francois.briere@insa-rouen.fr.
Jean-François
http://orcid.org/0000-0002-1381-4535
JF
Brière
D000596:Amino Acids / Q000737:chemistry; D002384:Catalysis; D004146:Dioxanes; D007555:Isoxazoles / Q000737:chemistry*; D013237:Stereoisomerism
D000596:Amino Acids; D004146:Dioxanes; D007555:Isoxazoles; C076489:Meldrum's acid
isoxazolidinone; phase-transfer catalysis; sulfanylation; synthetic methods; β-amino acid