ArticleThe Journal of organic chemistry2015
Asymmetric Redox-Annulation of Cyclic Amines.
Article in The Journal of organic chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed.
- Synthesis of Polycyclic Isoindolines via α-C-H/N-H Annulation of Alicyclic Amines.Organic letters · 2022Article
- Article
- α-C-H/N-H Annulation of Alicyclic Amines via Transient Imines: Preparation of Polycyclic Lactams.Organic letters · 2021Article
- 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
- 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
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
Cyclic amines such as 1,2,3,4-tetrahydroisoquinoline undergo regiodivergent annulation reactions with 4-nitrobutyraldehydes. These redox-neutral transformations enable the asymmetric synthesis of highly substituted polycyclic ring systems in just two steps from commercial materials. The utility of this process is illustrated in a rapid synthesis of (-)-protoemetinol. Computational studies provide mechanistic insights and implicate the elimination of acetic acid from an ammonium nitronate intermediate as the rate-determining step.
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