Premium
Enantioselective Phase‐Transfer Catalyzed α‐Sulfanylation of Isoxazolidin‐5‐ones: An Entry to β 2,2 ‐Amino Acid Derivatives
Author(s) -
Cadart Timothée,
Berthonneau Clément,
Levacher Vincent,
Perrio Stéphane,
Brière JeanFrançois
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603910
Subject(s) - enantioselective synthesis , electrophile , catalysis , chemistry , combinatorial chemistry , ammonium , brønsted–lowry acid–base theory , metathesis , organic chemistry , medicinal chemistry , polymerization , polymer
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 R 4 N + 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‐β 2,2 ‐amino acid derivatives.