ArticleAngewandte Chemie (International ed. in English)2018
Enantioselective Synthesis of N,S-Acetals by an Oxidative Pummerer-Type Transformation using Phase-Transfer Catalysis.
Article in Angewandte Chemie (International ed. in English), 2018. 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, 51 citations in OpenAlex.
- Stereoselective Generalizations over Diverse Sets of Chiral Acids Enabled by Buried Volume.Journal of the American Chemical Society · 2026Article
- A robust heterogeneous chiral phosphoric acid enables multi decagram scale production of optically activeGreen chemistry : an international journal and green chemistry resource : GC · 2024Article
- Interrogating the thionium hydrogen bond as a noncovalent stereocontrolling interaction in chiral phosphate catalysis.Chemical science · 2022Article
- Preparation of Thioaminals in Water.Molecules (Basel, Switzerland) · 2022Article
- New anionic cobalt(III) complexes enable enantioselective synthesis of spiro-fused oxazoline and iodoacetal derivatives.Frontiers in chemistry · 2022Article
- Modulation of Self-Separating Molecular Catalysts for Highly Efficient Biomass Transformations.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020Article
- Enantioselective aerobic oxidative cross-dehydrogenative coupling of glycine derivatives with ketones and aldehydesChemical science · 2020Article
- Quantitative Structure-Selectivity Relationships in Enantioselective Catalysis: Past, Present, and Future.Chemical reviews · 2020Review
- Enantioselective Kinetic Resolution/Desymmetrization ofAdvanced synthesis & catalysis · 2020Article
- Site-selective acylation of natural products with BINOL-derived phosphoric acids.ACS catalysis · 2019Article
- Bond-Forming and -Breaking Reactions at Sulfur(IV): Sulfoxides, Sulfonium Salts, Sulfur Ylides, and Sulfinate Salts.Chemical reviews · 2019Article
- Access to P-chiral phosphine oxides by enantioselective allylic alkylation of bisphenols.Chemical science · 2019Article
- Harnessing Noncovalent Interactions in Dual-Catalytic Enantioselective Heck-Matsuda Arylation.Journal of the American Chemical Society · 2019Article
- Enantioselective fluorination of homoallylic alcohols enabled by the tuning of non-covalent interactions.Chemical science · 2018Article
- Catalytic asymmetric synthesis of geminal-dicarboxylates.Chemical science · 2018Article
- Chiral Diaryliodonium Phosphate Enables Light Driven Diastereoselective α-C(spJournal of the American Chemical Society · 2018Article
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
Abstract
Reported is the first enantioselective oxidative Pummerer-type transformation using phase-transfer catalysis to deliver enantioenriched sulfur-bearing heterocycles. This reaction includes the direct oxidation of sulfides to a thionium intermediate, followed by an asymmetric intramolecular nucleophilic addition to form chiral cyclic N,S-acetals with moderate to high enantioselectivites. Deuterium-labelling experiments were performed to identify the stereodiscrimination step of this process. Further analysis of the reaction transition states, by means of multidimensional correlations and DFT calculations, highlight the existence of a set of weak noncovalent interactions between the catalyst and substrate that govern the enantioselectivity of the reaction.
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