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This review highlights the state of the art of the use of iminium ions as dienophiles in Aza-Diels–Alder (ADA) cycloadditions. An historical survey spanning the very first discovery of the reaction to modern developments, mechanistic studies and synthetic applications of the iminium variant of the ADA (iADA) reaction are presented. The discussion is focused on the intermolecular and intramolecular versions of the iADA reactions that are conducted in aqueous solutions to generate, in situ, the reactive dienophile from an amine hydrochloride and either aliphatic or aromatic aldehydes in the presence of a variety of dienes. The retro-ADA reaction is also presented as an interesting method for the protection of amines. The use of Lewis acid catalysis in these reactions was thoroughly studied by the reactions of different amines and aldehydes conducted in the presence of lanthanide(III) complexes.

Iminium Ions as Dienophiles in Aza-Diels–Alder Reactions: A Closer Look

MEMEO, MISAL GIUSEPPE;QUADRELLI, PAOLO
2012-01-01

Abstract

This review highlights the state of the art of the use of iminium ions as dienophiles in Aza-Diels–Alder (ADA) cycloadditions. An historical survey spanning the very first discovery of the reaction to modern developments, mechanistic studies and synthetic applications of the iminium variant of the ADA (iADA) reaction are presented. The discussion is focused on the intermolecular and intramolecular versions of the iADA reactions that are conducted in aqueous solutions to generate, in situ, the reactive dienophile from an amine hydrochloride and either aliphatic or aromatic aldehydes in the presence of a variety of dienes. The retro-ADA reaction is also presented as an interesting method for the protection of amines. The use of Lewis acid catalysis in these reactions was thoroughly studied by the reactions of different amines and aldehydes conducted in the presence of lanthanide(III) complexes.
2012
The Organic Chemistry/Polymer Science category includes resources concerned with the related fields of organic chemistry and polymer science. The organic chemistry resources deal with compounds of carbon with the exception of certain simple ones, such as the carbon oxides, carbonates, cyanides and cyanates (see Inorganic & Nuclear Chemistry). This category includes research on synthetic and natural organic compounds that may include other elements, such as hydrogen and oxygen, but also nitrogen, halogens, sulphur and phosphorous. Resources concerned with hydrocarbons, organic compounds containing only the elements carbon and hydrogen, are also included in this category. Examples are the alkanes, alkenes, alkynes and aromatics, such as benzene and naphthalene. Polymer science includes all resources dealing with the study, production and technology of polymers, which are compounds composed of very large molecules made up of repeating molecular units (monomers). Polymers may be natural substances, such as polysaccharides or proteins, or synthetic materials, such as nylon or polyethylene.
CHEMISTRY-A EUROPEAN JOURNAL
sì
000309238400001
2-s2.0-84867093373
Sì, ma tipo non specificato
Inglese
Internazionale
STAMPA
18
40
12554
12582
29
asymmetric synthesis; cycloaddition · Diels– Alder reactions; iminium ions; Lewis acids; mechanisms; synthetic methods
2
info:eu-repo/semantics/article
262
Memeo, MISAL GIUSEPPE; Quadrelli, Paolo
1 Contributo su Rivista::1.1 Articolo in rivista
none
1.1 Articolo in rivista
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11571/530445
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