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Synthesis of tetronic acid derivatives from novel active esters of α‐hydroxyacids
Author(s) -
Mitsos Christos,
Zografos Alexandras,
IgglessiMarkopoulou Olga
Publication year - 2002
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570390614
Subject(s) - chemistry , optically active , imide , methylene , condensation , organic chemistry , condensation reaction , stereochemistry , catalysis , physics , thermodynamics
Active esters, produced by condensation of O ‐acetyl protected α‐hydroxyacids with N ‐hydroxysuccin‐imide, react with anions of active methylene compounds to afford β,β‐tricarbonyl derivatives which upon deprotection undergo cyclization to 3‐alkoxycarbonyl and 3‐acyl tetronic acids. Incorporation of ( S )‐2‐ace‐toxyphenylacetic acid in this reaction sequence enables the synthesis of optically active 5‐phenyltetronic acid derivatives.