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Organocatalyzed Synthesis of Isoxazolidin‐5‐ones: The Meldrum’s Acid Approach
Author(s) -
Postikova Svetlana,
Tite Tony,
Levacher Vincent,
Brière JeanFrançois
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201300465
Subject(s) - chemistry , ketene , domino , decarboxylation , meldrum's acid , nitrone , cycloaddition , organocatalysis , pericyclic reaction , base (topology) , organic chemistry , combinatorial chemistry , catalysis , enantioselective synthesis , mathematical analysis , mathematics
Meldrum’s acid has turned out to be a useful ketene equivalent when faced to nitrone dipoles to form various isoxazolidin‐5‐one derivatives under very mild Brønsted base organocatalytic conditions. The first asymmetric version of this original domino anionic formal [3+2] cycloaddition–decarboxylation reaction was demonstrated by means of quinine‐based organocatalysts.