ArticleChemical science2018
Synergistic formal ring contraction for the enantioselective synthesis of spiropyrazolones.
Article in Chemical science, 2018. 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, 57 citations in OpenAlex.
- The Diarylprolinol Silyl Ethers: After 20 Years Still Opening New Doors in Asymmetric Catalysis.Angewandte Chemie (International ed. in English) · 2026Review
- Enantioselective Synthesis of Spirocyclic Isoxazolones Using a Conia-Ene Type Reaction.The Journal of organic chemistry · 2025Article
- Enantioselective Preparation of Cyclopentene-Based Amino Acids with a Quaternary Carbon Center.The Journal of organic chemistry · 2024Article
- Atropostatin: Design and Total Synthesis of an Atropisomeric Lactone-Atorvastatin Prodrug.Molecules (Basel, Switzerland) · 2023Article
- Cooperative Palladium/Isothiourea Catalyzed Enantioselective Formal (3+2) Cycloaddition of Vinylcyclopropanes and α,β-Unsaturated Esters.Angewandte Chemie (International ed. in English) · 2022Article
- Recent progress in asymmetric synergistic catalysis - the judicious combination of selected chiral aminocatalysts with achiral metal catalysts.Organic & biomolecular chemistry · 2022Review
- Studying the reactivity of alkyl substituted BODIPYs: first enantioselective addition of BODIPY to MBH carbonates.Chemical science · 2021Article
- Identifying reactive intermediates by mass spectrometry.Chemical science · 2020Review
- Enamine/Transition Metal Combined Catalysis: Catalytic Transformations Involving Organometallic Electrophilic Intermediates.Topics in current chemistry (Cham) · 2019Review
- Determination of the absolute configuration of conformationally flexible molecules by simulation of chiro-optical spectra: a case study.RSC advances · 2019Article
- Proline bulky substituents consecutively act as steric hindrances and directing groups in a Michael/Conia-ene cascade reaction under synergistic catalysis.Chemical science · 2019Article
Corrections and comments
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Authors and funding
8 authors at 3 institutions in 3 countries.
Funding
No grant is acknowledged in the PubMed record.
Abstract
The rapid generation of molecular complexity from simple reactants is a key challenge in organic synthesis. Spiro compounds, underrepresented 3D motifs in chemical libraries, represent a challenge due to the creation of spiro quaternary carbon and the need to control the 3D shape in one step. Herein, we report the first ring contraction/formal [6 + 2] cycloaddition using synergistic Pd(0)/secondary amine catalysis, obtaining [5,5]-spiropyrazolone derivatives in excellent yields and stereoselectivities. We demonstrate that this reaction has a broad scope of early and late stage derivatization that will benefit the creation of highly valuable chemical libraries using spiropyrazolone motifs. We detected the key palladium activated intermediate in its protonated form by mass spectrometry and characterized its structure by infrared spectroscopy and DFT calculations, allowing us to propose a conceivable mechanistic pathway for this reaction.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.