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- Aza-Cope_rearrangement abstract "Rearrangements, especially those that can participate in cascade reactions, such as the aza-Cope rearrangements, are of high practical as well as conceptual importance in organic chemistry, due to their ability to quickly build structural complexity out of simple starting materials. The aza-Cope rearrangements are examples of heteroatom versions of the Cope rearrangement, which is a [3,3]-sigmatropic rearrangement that shifts single and double bonds between two allylic components. In accordance with the Woodward-Hoffman rules, thermal aza-Cope rearrangements proceed suprafacially. Aza-Cope rearrangements are generally classified by the position of the nitrogen in the molecule (see figure): The first example of an aza-Cope rearrangement was the ubiquitous cationic 2-aza-Cope Rearrangement, which takes place at temperatures 100-200 °C lower than the Cope rearrangement due to the facile nature of the rearrangement. The facile nature of this rearrangement is attributed both to the fact that the cationic 2-aza-Cope is inherently thermoneutral, meaning there's no bias for the starting material or product, as well as to the presence of the charged heteroatom in the molecule, which lowers the activation barrier. Less common are the 1-aza-Cope rearrangement and the 3-aza-Cope rearrangement, which are the microscopic reverse of each other. The 1- and 3-aza-Cope rearrangements have high activation barriers and limited synthetic applicability, accounting for their relative obscurity.To maximize its synthetic utility, the cationic 2-aza-Cope rearrangement is normally paired with a thermodynamic bias toward one side of the rearrangement. The most common and synthetically useful strategy couples the cationic 2-aza-Cope rearrangement with a Mannich cyclization, and is the subject of much of this article. This tandem aza-Cope/Mannich reaction is characterized by its mild reaction conditions, diastereoselectivity, and wide synthetic applicability. It provides easy access to acyl-substituted pyrrolidines, a structure commonly found in natural products such as alkaloids, and has been used in the synthesis of a number of them, notably strychnine and crinine.Larry E. Overman and coworkers have done extensive research on this reaction.".
- Aza-Cope_rearrangement wikiPageID "43256469".
- Aza-Cope_rearrangement wikiPageLength "50657".
- Aza-Cope_rearrangement wikiPageOutDegree "80".
- Aza-Cope_rearrangement wikiPageRevisionID "695700026".
- Aza-Cope_rearrangement wikiPageWikiLink Alkaloid.
- Aza-Cope_rearrangement wikiPageWikiLink Alkanolamine.
- Aza-Cope_rearrangement wikiPageWikiLink Alkylimino-de-oxo-bisubstitution.
- Aza-Cope_rearrangement wikiPageWikiLink Allyl.
- Aza-Cope_rearrangement wikiPageWikiLink Amaryllidaceae.
- Aza-Cope_rearrangement wikiPageWikiLink Annulation.
- Aza-Cope_rearrangement wikiPageWikiLink Camphorsulfonic_acid.
- Aza-Cope_rearrangement wikiPageWikiLink Cascade_reaction.
- Aza-Cope_rearrangement wikiPageWikiLink Category:Name_reactions.
- Aza-Cope_rearrangement wikiPageWikiLink Category:Rearrangement_reactions.
- Aza-Cope_rearrangement wikiPageWikiLink Cope_rearrangement.
- Aza-Cope_rearrangement wikiPageWikiLink Crinine.
- Aza-Cope_rearrangement wikiPageWikiLink Cyanamide.
- Aza-Cope_rearrangement wikiPageWikiLink Enol.
- Aza-Cope_rearrangement wikiPageWikiLink Formaldehyde.
- Aza-Cope_rearrangement wikiPageWikiLink Indole.
- Aza-Cope_rearrangement wikiPageWikiLink Indolizidine.
- Aza-Cope_rearrangement wikiPageWikiLink Larry_E._Overman.
- Aza-Cope_rearrangement wikiPageWikiLink Lithium_aluminium_hydride.
- Aza-Cope_rearrangement wikiPageWikiLink Organic_chemistry.
- Aza-Cope_rearrangement wikiPageWikiLink Organolithium_reagent.
- Aza-Cope_rearrangement wikiPageWikiLink Pinacol_rearrangement.
- Aza-Cope_rearrangement wikiPageWikiLink Piperidine.
- Aza-Cope_rearrangement wikiPageWikiLink Pyridine.
- Aza-Cope_rearrangement wikiPageWikiLink Pyrrole.
- Aza-Cope_rearrangement wikiPageWikiLink Pyrrolidine.
- Aza-Cope_rearrangement wikiPageWikiLink Pyrrolizidine.
- Aza-Cope_rearrangement wikiPageWikiLink Reductive_amination.
- Aza-Cope_rearrangement wikiPageWikiLink Siegfried_Blechert.
- Aza-Cope_rearrangement wikiPageWikiLink Sigmatropic_reaction.
- Aza-Cope_rearrangement wikiPageWikiLink Stemona.
- Aza-Cope_rearrangement wikiPageWikiLink Strychnine.
- Aza-Cope_rearrangement wikiPageWikiLink Strychnine_total_synthesis.
- Aza-Cope_rearrangement wikiPageWikiLink Strychnos.
- Aza-Cope_rearrangement wikiPageWikiLink Tert-Butyl_hydroperoxide.
- Aza-Cope_rearrangement wikiPageWikiLink Umpolung.
- Aza-Cope_rearrangement wikiPageWikiLink Wittig_reaction.
- Aza-Cope_rearrangement wikiPageWikiLink File:1_and_3_aza_cope_rearrangements.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:1_aza_cope_rearrangement.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:3_aza_cope_rearrangement.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Amine_alkylation.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Aza-cope_intropicture_final.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:AzaCopeMannich_generic.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Aza_cope_aza_prins_final.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Bond_rotation_aza_cope.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Cationic_2_aza_cope_final_general.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Crinine_aza_cope.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Cyanomethyl_azacope.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Diradical_transition_state_aza_cope.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Epoxide_ring_opening_aza_cope.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Fowler_modification_aza_cope.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Horowitz_geissman_final.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Horowitz_geissman_first.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Organolithium_final.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Oxazolidines_final_aza_cope.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Oxycopefor_the_azacope.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Precursors_to_strychnine_final.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Ring_strain_1_aza_cope.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Seven_membered_aza_cope_final.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Sime_aza_cope_trap.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Sm_scope_aza_cope_final.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Stereochem_E_vs_Z_aza_cope.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Stereochem_anti_vs_syn_on_ring_aza_cope.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Strychnine_aza_cope_step_finalll.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Strychnine_final_retrosynth.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Tricyclic_final.tiff.
- Aza-Cope_rearrangement wikiPageWikiLink File:Zwitterionic_3_aza_cope_final.tiff.
- Aza-Cope_rearrangement wikiPageWikiLinkText "Aza-Cope rearrangement".
- Aza-Cope_rearrangement wikiPageUsesTemplate Template:Orphan.
- Aza-Cope_rearrangement wikiPageUsesTemplate Template:Reflist.
- Aza-Cope_rearrangement subject Category:Name_reactions.
- Aza-Cope_rearrangement subject Category:Rearrangement_reactions.
- Aza-Cope_rearrangement comment "Rearrangements, especially those that can participate in cascade reactions, such as the aza-Cope rearrangements, are of high practical as well as conceptual importance in organic chemistry, due to their ability to quickly build structural complexity out of simple starting materials. The aza-Cope rearrangements are examples of heteroatom versions of the Cope rearrangement, which is a [3,3]-sigmatropic rearrangement that shifts single and double bonds between two allylic components.".
- Aza-Cope_rearrangement label "Aza-Cope rearrangement".
- Aza-Cope_rearrangement sameAs Q17085416.
- Aza-Cope_rearrangement sameAs m.0zg75dy.
- Aza-Cope_rearrangement sameAs Q17085416.
- Aza-Cope_rearrangement wasDerivedFrom Aza-Cope_rearrangement?oldid=695700026.
- Aza-Cope_rearrangement isPrimaryTopicOf Aza-Cope_rearrangement.