ArticleNature communications2016
Enantioselective acyl transfer catalysis by a combination of common catalytic motifs and electrostatic interactions.
Article in Nature communications, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 12 papers.
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Who cites it
12 citing papers in PubMed.
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- Computational Library Enables Pattern Recognition of Noncovalent Interactions and Application as a Modern Linear Free Energy Relationship.The Journal of organic chemistry · 2024Article
- Intramolecular Carboxyamidation of Alkyne-Tethered O-Acylhydroxamates through Formation of Fe(III)-Nitrenoids.Chemistry (Weinheim an der Bergstrasse, Germany) · 2024Article
- A chiral pentanidium and pyridinyl-sulphonamide ion pair as an enantioselective organocatalyst for Steglich rearrangement.Chemical science · 2023Article
- Strategic Design and Synthesis of Ferrocene Linked Porous Organic Frameworks toward Tunable COInternational journal of molecular sciences · 2023Article
- Silver/chiral pyrrolidinopyridine relay catalytic cycloisomerization/(2 + 3) cycloadditions of enynamides to asymmetrically synthesize bispirocyclopentenes as PDE1B inhibitors.Communications chemistry · 2023Article
- Semisynthetic Sesquiterpene Lactones Generated by the Sensibility of Glaucolide B to Lewis and Brønsted-Lowry Acids and Bases: Cytotoxicity and Anti-Inflammatory Activities.Molecules (Basel, Switzerland) · 2023Article
- Synthesis of Carvone Derivatives and In Silico and In Vitro Screening of Anti-Inflammatory Activity in Murine Macrophages.International journal of molecular sciences · 2023Article
- Green Chemistry Meets Asymmetric Organocatalysis: A Critical Overview on Catalysts Synthesis.ChemSusChem · 2021Review
- Enantiocontrol by assembled attractive interactions in copper-catalyzed asymmetric direct alkynylation of α-ketoesters with terminal alkynes: OH···O/spChemical science · 2018Article
- Alkylative kinetic resolution of vicinal diols under phase-transfer conditions: a chiral ammonium borinate catalysis.Chemical science · 2018Article
- DMAP-assisted sulfonylation as an efficient step for the methylation of primary amine motifs on solid support.Beilstein journal of organic chemistry · 2017Article
Corrections and comments
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Authors and funding
7 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Catalysts that can promote acyl transfer processes are important to enantioselective synthesis and their development has received significant attention in recent years. Despite noteworthy advances, discovery of small-molecule catalysts that are robust, efficient, recyclable and promote reactions with high enantioselectivity can be easily and cost-effectively prepared in significant quantities (that is, >10 g) has remained elusive. Here, we demonstrate that by attaching a binaphthyl moiety, appropriately modified to establish H-bonding interactions within the key intermediates in the catalytic cycle, and a 4-aminopyridyl unit, exceptionally efficient organic molecules can be prepared that facilitate enantioselective acyl transfer reactions. As little as 0.5 mol% of a member of the new catalyst class is sufficient to generate acyl-substituted all-carbon quaternary stereogenic centres in quantitative yield and in up to 98:2 enantiomeric ratio (er) in 5 h. Kinetic resolution or desymmetrization of 1,2-diol can be performed with high efficiency and enantioselectivity as well.
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