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Direct α‐Functionalization of Saturated Cyclic Amines

Identifieur interne : 000903 ( Main/Exploration ); précédent : 000902; suivant : 000904

Direct α‐Functionalization of Saturated Cyclic Amines

Auteurs : Emily A. Mitchell ; Aldo Peschiulli ; Nicolas Lefevre ; Lieven Meerpoel [Belgique] ; Bert U. W. Maes [Belgique]

Source :

RBID : ISTEX:D822348DEEE3894D374A978B9BB7FF635733E21A

Descripteurs français

English descriptors

Abstract

Recent advances in synthetic methods for the direct α‐functionalization of saturated cyclic amines are described. Methods are categorized according to the in situ formed reactive intermediate (α‐amino cation, α‐amino anion, and α‐amino radical). Transition‐metal‐catalyzed reactions involving other intermediates have been treated as a separate and fourth class.

Url:
DOI: 10.1002/chem.201201539


Affiliations:


Links toward previous steps (curation, corpus...)


Le document en format XML

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<term>Allyl</term>
<term>Allyl bromide</term>
<term>Allylation</term>
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<term>Anodic</term>
<term>Anodic oxidation</term>
<term>Antwerp</term>
<term>Aryl</term>
<term>Aryl bromides</term>
<term>Arylation</term>
<term>Arylboronate ester</term>
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<term>Asymmetric deprotonation</term>
<term>Asymmetric synthesis</term>
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<term>Beng</term>
<term>Benzylic</term>
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<term>Bu3sncl</term>
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<term>Carbophilic iprauotf</term>
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<term>Chiral ligands</term>
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<term>Methyl alkyl ketones</term>
<term>Methyl group</term>
<term>Moderate yields</term>
<term>Moiety</term>
<term>Molecular oxygen</term>
<term>Molecular sieves</term>
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<term>More reactive</term>
<term>Morpholine</term>
<term>Natural products</term>
<term>Nbuli</term>
<term>Negishi</term>
<term>Nitroalkanes</term>
<term>Nitromethane</term>
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<term>Nucleophiles</term>
<term>Nucleophilic</term>
<term>Nucleophilic species</term>
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<term>Photocatalyst</term>
<term>Pinacol ester</term>
<term>Piperazine</term>
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<term>Piperidine derivatives</term>
<term>Piperidines</term>
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<term>Pretreated</term>
<term>Product formation</term>
<term>Product ratio</term>
<term>Protocol</term>
<term>Pyrroles</term>
<term>Pyrrolidine</term>
<term>Pyrrolidine derivatives</term>
<term>Pyrrolidine systems</term>
<term>Pyrrolidines</term>
<term>Quenching</term>
<term>Racemic</term>
<term>Radical intermediates</term>
<term>Rate constants</term>
<term>Reaction conditions</term>
<term>Reaction mechanism</term>
<term>Reaction mixture</term>
<term>Reaction time</term>
<term>Reactive</term>
<term>Reactivity series</term>
<term>Reagent</term>
<term>Review scheme</term>
<term>Ring closure</term>
<term>Ring size</term>
<term>Room temperature</term>
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<term>Scheme scheme</term>
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<term>Verlag gmbh</term>
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<term>Alkaloid</term>
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<term>Allyl bromide</term>
<term>Allylation</term>
<term>Amination</term>
<term>Amine</term>
<term>Analogue</term>
<term>Angew</term>
<term>Anion</term>
<term>Anodic</term>
<term>Anodic oxidation</term>
<term>Antwerp</term>
<term>Aryl</term>
<term>Aryl bromides</term>
<term>Arylation</term>
<term>Arylboronate ester</term>
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<term>Asymmetric deprotonation</term>
<term>Asymmetric synthesis</term>
<term>Axial position</term>
<term>Basl</term>
<term>Beng</term>
<term>Benzylic</term>
<term>Better understanding</term>
<term>Bispidine</term>
<term>Bromide</term>
<term>Bu3sncl</term>
<term>Campos</term>
<term>Carbanion</term>
<term>Carbophilic iprauotf</term>
<term>Catalysis</term>
<term>Catalyst</term>
<term>Catalytic</term>
<term>Catalytic cycle</term>
<term>Cation</term>
<term>Cation pool</term>
<term>Cf3cooh</term>
<term>Chair conformation</term>
<term>Chem</term>
<term>Chemical oxidant</term>
<term>Chiral</term>
<term>Chiral ligand</term>
<term>Chiral ligands</term>
<term>Closure</term>
<term>Co2me</term>
<term>Coldham</term>
<term>Commun</term>
<term>Cooling cycle</term>
<term>Cyanation</term>
<term>Cyanide</term>
<term>Cyclic</term>
<term>Cyclic amines</term>
<term>Cyclic amines review scheme</term>
<term>Cyclic amines scheme</term>
<term>Deprotonation</term>
<term>Derivative</term>
<term>Dialkyl</term>
<term>Dialkyl malonates</term>
<term>Dialkyl phosphonates</term>
<term>Diamine</term>
<term>Diastereomeric</term>
<term>Diastereomeric complexes</term>
<term>Diastereomers</term>
<term>Diastereoselective</term>
<term>Diastereoselective deprotonation</term>
<term>Diastereoselectivity</term>
<term>Direct cyanation</term>
<term>Direct functionalization</term>
<term>Dynamic resolution</term>
<term>Electrochemical oxidation</term>
<term>Electrophile</term>
<term>Electrophiles</term>
<term>Electrophilic</term>
<term>Electrophilic species</term>
<term>Enantioenriched</term>
<term>Enantiomer</term>
<term>Enantiomeric</term>
<term>Enantiomeric ratio</term>
<term>Enantiomeric ratios</term>
<term>Enantiomerization</term>
<term>Enantioselective</term>
<term>Enantioselective synthesis</term>
<term>Enantioselectivity</term>
<term>Equatorial</term>
<term>Equatorial position</term>
<term>Equiv</term>
<term>Equiv cf3cooh</term>
<term>Ester</term>
<term>Ether</term>
<term>External oxidant</term>
<term>Eyring plots</term>
<term>Functionality</term>
<term>Functionalization</term>
<term>Functionalized</term>
<term>Gawley</term>
<term>Gmbh</term>
<term>Good enantioselectivity</term>
<term>Good yields</term>
<term>Green chem</term>
<term>Heteroaryl bromides</term>
<term>Heterocyclic chemistry</term>
<term>High yields</term>
<term>Hydride shift</term>
<term>Iminium</term>
<term>Iminium ions</term>
<term>Iminium salt</term>
<term>Indole</term>
<term>Insertion</term>
<term>Intramolecular</term>
<term>Intramolecular amination</term>
<term>Inversion</term>
<term>Iprli</term>
<term>Kainic acid</term>
<term>Ketone</term>
<term>Kgaa</term>
<term>Leonori</term>
<term>Lett</term>
<term>Lewis acid</term>
<term>Lewis acid catalyst</term>
<term>Ligand</term>
<term>Lithiated</term>
<term>Lithiated species</term>
<term>Lithiation</term>
<term>Lithium</term>
<term>Lithium transmetallation</term>
<term>Maes</term>
<term>Major enantiomer</term>
<term>Major product</term>
<term>Malonates</term>
<term>Mannich</term>
<term>Mechanistic</term>
<term>Methanol</term>
<term>Methodology</term>
<term>Methyl</term>
<term>Methyl alkyl ketones</term>
<term>Methyl group</term>
<term>Moderate yields</term>
<term>Moiety</term>
<term>Molecular oxygen</term>
<term>Molecular sieves</term>
<term>Mono</term>
<term>More reactive</term>
<term>Morpholine</term>
<term>Natural products</term>
<term>Nbuli</term>
<term>Negishi</term>
<term>Nitroalkanes</term>
<term>Nitromethane</term>
<term>Nucleophile</term>
<term>Nucleophiles</term>
<term>Nucleophilic</term>
<term>Nucleophilic species</term>
<term>Optimized</term>
<term>Optimized conditions</term>
<term>Organolithium</term>
<term>Organolithium complexes</term>
<term>Oxidant</term>
<term>Oxidative</term>
<term>Oxidative addition</term>
<term>Oxidative mannich reaction</term>
<term>Oxidative reaction</term>
<term>Pathway</term>
<term>Ph2co</term>
<term>Phenyl</term>
<term>Phenyl group</term>
<term>Phenyl ring</term>
<term>Phnco</term>
<term>Photocatalyst</term>
<term>Pinacol ester</term>
<term>Piperazine</term>
<term>Piperidine</term>
<term>Piperidine derivatives</term>
<term>Piperidines</term>
<term>Poor results</term>
<term>Pretreated</term>
<term>Product formation</term>
<term>Product ratio</term>
<term>Protocol</term>
<term>Pyrroles</term>
<term>Pyrrolidine</term>
<term>Pyrrolidine derivatives</term>
<term>Pyrrolidine systems</term>
<term>Pyrrolidines</term>
<term>Quenching</term>
<term>Racemic</term>
<term>Radical intermediates</term>
<term>Rate constants</term>
<term>Reaction conditions</term>
<term>Reaction mechanism</term>
<term>Reaction mixture</term>
<term>Reaction time</term>
<term>Reactive</term>
<term>Reactivity series</term>
<term>Reagent</term>
<term>Review scheme</term>
<term>Ring closure</term>
<term>Ring size</term>
<term>Room temperature</term>
<term>Sbuli</term>
<term>Scheme</term>
<term>Scheme scheme</term>
<term>Selectivity</term>
<term>Sime3</term>
<term>Sparteine</term>
<term>Stereoselectivity</term>
<term>Steric</term>
<term>Steric bulk</term>
<term>Stoichiometric</term>
<term>Stoichiometric quantities</term>
<term>Stoichiometric quantity</term>
<term>Substituent</term>
<term>Sulfamoyloxymethyl substituent</term>
<term>Tbhp</term>
<term>Tertiary</term>
<term>Tertiary amines</term>
<term>Tertiary cyclic amines</term>
<term>Tetrahedron</term>
<term>Tetrahedron lett</term>
<term>Tetrahydroisoquinoline</term>
<term>Tetrahydroisoquinolines</term>
<term>Thermal oxidation</term>
<term>Thermodynamic</term>
<term>Thermodynamic data</term>
<term>Thermodynamic parameters</term>
<term>Thermodynamic resolution</term>
<term>Tmeda</term>
<term>Tmscl</term>
<term>Tour mechanism</term>
<term>Trans</term>
<term>Transition metals</term>
<term>Transmetallation</term>
<term>Verlag</term>
<term>Verlag gmbh</term>
<term>Weinheim</term>
<term>Weinheim chem</term>
<term>Wide variety</term>
<term>Zhang</term>
<term>Zhou</term>
<term>Zncl2</term>
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<front>
<div type="abstract" xml:lang="en">Recent advances in synthetic methods for the direct α‐functionalization of saturated cyclic amines are described. Methods are categorized according to the in situ formed reactive intermediate (α‐amino cation, α‐amino anion, and α‐amino radical). Transition‐metal‐catalyzed reactions involving other intermediates have been treated as a separate and fourth class.</div>
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