1,2-Dioxo-3-isopropyloxy-4-methyl-3-cyclobutene as a nucleophilic synthon. Synthesis of Sq-containing cinnamic acid derivatives

An enolate-like intermediate A derived from 1,2-dioxo-3-isopropyloxy-4-methyl-3-cyclobutene ( 6 ) has proven to be a novel nucleophilic synthon for an aldol condensation reaction with an arylaldehyde to give a variety of 4-hydroxy-2,3-dioxocyclobut-1-enyl group (Sq group)-containing cinnamic acid de...

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Bibliographic Details
Published inTetrahedron letters Vol. 43; no. 38; pp. 6755 - 6758
Main Authors Shinada, Tetsuro, Ooyama, Yuuki, Hayashi, Ken-ichi, Ohfune, Yasufumi
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 16.09.2002
Elsevier
Subjects
aldol condensation
Chemistry
Chemistry, Organic
cinnamic acids
nucleophilic synthon
Physical Sciences
Science & Technology
squaric acid
squaric acid
aldol condensation
cinnamic acids
nucleophilic synthon
RING-EXPANSION
UNSATURATED ORGANOSILANES
1,2-ADDITION
POLYFUNCTIONALIZED CARBOCYCLES
REARRANGEMENT
HIGHLY SELECTIVE SYNTHESIS
HETEROCYCLES
CYCLOBUTENEDIONE MONOACETALS
ESTERS
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Summary:An enolate-like intermediate A derived from 1,2-dioxo-3-isopropyloxy-4-methyl-3-cyclobutene ( 6 ) has proven to be a novel nucleophilic synthon for an aldol condensation reaction with an arylaldehyde to give a variety of 4-hydroxy-2,3-dioxocyclobut-1-enyl group (Sq group)-containing cinnamic acid derivatives. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01525-3