ArticleJournal of the American Chemical Society2012
Enantioselective organo-SOMO cycloadditions: a catalytic approach to complex pyrrolidines from olefins and aldehydes.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 11 papers.
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Who cites it
11 citing papers in PubMed.
- Enantioselective radical chemistry: a bright future ahead.Beilstein journal of organic chemistry · 2025Article
- 1,5-Hydrogen atom transfer of α-iminyl radical cations: a new platform for relay annulation for pyridine derivatives and axially chiral heterobiaryls.Chemical science · 2024Article
- KOtBu-catalysed α-homoallylic alkylation of acyclic amides with 1-aryl-1,3-dienes.Molecular diversity · 2023Article
- Two Paths to Oxidative C-H Amination Under Basic Conditions: A Theoretical Case Study Reveals Hidden Opportunities Provided by Electron Upconversion.Chemistry (Weinheim an der Bergstrasse, Germany) · 2022Article
- Enantioselective, Decarboxylative (3+2)-Cycloaddition of Azomethine Ylides and Chromone-3-Carboxylic Acids.Molecules (Basel, Switzerland) · 2022Article
- A Rh(III)-Catalyzed Formal [4+1] Approach to Pyrrolidines from Unactivated Terminal Alkenes and Nitrene Sources.Journal of the American Chemical Society · 2019Article
- Direct, enantioselective α-alkylation of aldehydes using simple olefins.Nature chemistry · 2017Article
- Synthesis of 2-Aryl- and 2-Vinylpyrrolidines via Copper-Catalyzed Coupling of Styrenes and Dienes with Potassium β-Aminoethyl Trifluoroborates.Organic letters · 2016Article
- Catalytic Radical Domino Reactions in Organic Synthesis.ACS catalysis · 2014Article
- Enantioselective intramolecular aldehyde α-alkylation with simple olefins: direct access to homo-ene products.Journal of the American Chemical Society · 2013Article
- Cascade radical reaction of substrates with a carbon-carbon triple bond as a radical acceptor.Beilstein journal of organic chemistry · 2013Article
Corrections and comments
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Authors and funding
4 authors.
Funding
Abstract
A new method to rapidly generate pyrrolidines via a SOMO-activated enantioselective (3 + 2) coupling of aldehydes and conjugated olefins has been accomplished. A radical-polar crossover mechanism is proposed wherein olefin addition to a transient enamine radical cation and oxidation of the resulting radical furnish a cationic intermediate which is vulnerable to nucleophilic addition of a tethered amine group. A range of olefins, including styrenes and dienes, are shown to provide stereochemically complex pyrrolidine products with high chemical efficiency and enantiocontrol.
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