ArticleAngewandte Chemie (International ed. in English)2014
Catalytic asymmetric synthesis of 8-oxabicyclooctanes by intermolecular [5+2] pyrylium cycloadditions.
Article in Angewandte Chemie (International ed. in English), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 95 citations in OpenAlex.
- Catalytic Enantioselective Synthesis of 1,1-Disubstituted Isochromans.Journal of the American Chemical Society · 2026Article
- AlkynylThe Journal of organic chemistry · 2025Article
- An Unexpected Formation of Spiro Isoxazoline-Dihydrofurane Compounds from Substituted Ketofurfuryl Alcohols.Molecules (Basel, Switzerland) · 2024Article
- Enantioselective dearomatization reactions of heteroarenes by anion-binding organocatalysis.Chemical communications (Cambridge, England) · 2023Review
- Highly Diastereoselective Intramolecular Asymmetric Oxidopyrylium-olefin [5 + 2] Cycloaddition and Synthesis of 8-Oxabicyclo[3.2.1]oct-3-enone Containing Ring Systems.The Journal of organic chemistry · 2021Article
- Investigations into a Stoichiometrically Equivalent Intermolecular Oxidopyrylium [5 + 2] Cycloaddition Reaction Leveraging 3-Hydroxy-4-pyrone-Based Oxidopyrylium Dimers.The Journal of organic chemistry · 2021Article
- Helical Multi-Coordination Anion-Binding Catalysts for the Highly Enantioselective Dearomatization of Pyrylium Derivatives.Angewandte Chemie (International ed. in English) · 2019Article
- Catalytic Enantioselective Intermolecular [5 + 2] Dipolar Cycloadditions of a 3-Hydroxy-4-pyrone-Derived Oxidopyrylium Ylide.Organic letters · 2017Article
- Asymmetric syntheses of 8-oxabicyclo[3,2,1]octane and 11-oxatricyclo[5.3.1.0]undecane from glycals.Chemical science · 2017Article
- Racemic hemiacetals as oxygen-centered pronucleophiles triggering cascade 1,4-addition/Michael reaction through dynamic kinetic resolution under iminium catalysis. Development and mechanistic insights.Chemical science · 2017Article
- Achmatowicz Reaction and its Application in the Syntheses of Bioactive Molecules.RSC advances · 2016Article
- (Thio)urea-mediated synthesis of functionalized six-membered rings with multiple chiral centers.Beilstein journal of organic chemistry · 2016Review
- Enantioselective Copper(I)-Catalyzed Alkynylation of Oxocarbenium Ions to Set Diaryl Tetrasubstituted Stereocenters.Angewandte Chemie (International ed. in English) · 2015Article
- A Simple Primary Amine Catalyst for Enantioselective α-Hydroxylations and α-Fluorinations of Branched Aldehydes.Organic letters · 2015Article
- Enantioselective copper-catalyzed alkynylation of benzopyranyl oxocarbenium ions.The Journal of organic chemistry · 2015Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
Highly enantioselective intermolecular [5+2] cycloadditions of pyrylium ion intermediates with electron-rich alkenes are promoted by a dual catalyst system composed of an achiral thiourea and a chiral primary aminothiourea. The observed enantioselectivity is highly dependent on the substitution pattern of the 5π component, and the basis for this effect is analyzed using experimental and computational evidence. The resultant 8-oxabicyclo[3.2.1]octane derivatives possess a scaffold common in natural products and medicinally active compounds and are also versatile chiral building blocks for further manipulations. Several stereoselective complexity-generating transformations of the 8-oxabicyclooctane products are presented.
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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.