ArticleChemistry (Weinheim an der Bergstrasse, Germany)2015
Intramolecular Redox-Mannich Reactions: Facile Access to the Tetrahydroprotoberberine Core.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 17 papers.
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Who cites it
17 citing papers in PubMed.
- Intramolecular Phosphine-Promoted Knoevenagel Based Redox-Reaction.Molecules (Basel, Switzerland) · 2022Article
- Article
- C-H Bond Functionalization of Amines: A Graphical Overview of Diverse Methods.SynOpen (2017) · 2021Article
- Redox-Annulations of Cyclic Amines withOrganic letters · 2020Article
- Traceless Redox-Annulations of Alicyclic Amines.SynOpen (2017) · 2020Article
- Redox-Annulations of Cyclic Amines with Electron-Deficient o-Tolualdehydes.Organic letters · 2019Article
- B(COrganic letters · 2019Article
- Regio- and Enantioselective (Het)arylation of β-Alkenyl Pyrroline to α-Aryl-β-alkenyl Pyrrolidines.ACS omega · 2019Article
- Highly diastereoselective synthesis of tricyclic fused-pyrans by sequential hydride shift mediated double C(spChemical science · 2018Article
- Redox-Annulations of Cyclic Amines with 2-(2-Oxoethyl)malonates.Organic letters · 2018Article
- Decarboxylative Annulation of α-Amino Acids with β-Ketoaldehydes.Organic letters · 2018Article
- Synthesis of Polycyclic Imidazolidinones via Amine Redox-Annulation.Organic letters · 2017Article
- Acetic Acid Promoted Redox Annulations with Dual C-H Functionalization.Organic letters · 2017Article
- Redox-Neutral Aromatization of Cyclic Amines: Mechanistic Insights and Harnessing of Reactive Intermediates for Amine α- and β-C-H Functionalization.Chemistry (Weinheim an der Bergstrasse, Germany) · 2016Article
- Decarboxylative Annulation of α-Amino Acids with γ-Nitroaldehydes.Organic letters · 2016Article
- Redox-Annulation of Cyclic Amines and β-Ketoaldehydes.Organic letters · 2016Article
- An Ugi Reaction Incorporating a Redox-Neutral Amine C-H Functionalization Step.Organic letters · 2016Article
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2 authors.
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Abstract
Cyclic amines such as pyrrolidine undergo redox-annulations with 2-formylaryl malonates. Concurrent oxidative amine α-CH bond functionalization and reductive N-alkylation render this transformation redox-neutral. This redox-Mannich process provides regioisomers of classic Reinhoudt reaction products as an entry to the tetrahydroprotoberberine core, enabling the synthesis of (±)-thalictricavine and its epimer. An unusually mild amine-promoted dealkoxycarbonylation was discovered in the course of these studies.
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