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Second Generation Protocol for Multicomponent Coupling Reactions of Aldehydes, Amides and Dienophiles
Author(s) -
Klaus Stefan,
Hübner Sandra,
Neumann Helfried,
Strübing Dirk,
von Wangelin Axel Jacobi,
Gördes Dirk,
Beller Matthias
Publication year - 2004
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.200404056
Subject(s) - chemistry , reagent , yield (engineering) , coupling reaction , aldehyde , organic chemistry , condensation reaction , condensation , reaction conditions , combinatorial chemistry , catalysis , materials science , physics , metallurgy , thermodynamics
An improved one‐pot procedure for the three‐component coupling reaction of aldehydes, amides and dienophiles (AAD reaction) has been developed. Compared to known protocols for this type of reaction, the use of aromatic solvents in the presence of dehydrating reagents allows an efficient synthesis of previously not accessible products. Condensation of ubiquitous available aldehydes and amides and subsequent Diels–Alder reactions with dienophiles furnishes endo ‐selective amino‐functionalized hexahydroisoindole‐1,3‐dione and tetrahydrophthalic acid derivatives in good yield.