ReviewChemical science2020
Stereospecific nucleophilic substitution at tertiary and quaternary stereocentres.
Review in Chemical science, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
What it found
Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.
The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.
Who cites it
15 citing papers in PubMed, 49 citations in OpenAlex.
- The catalytic enantioselective [1,2]-Wittig rearrangement cascade of allylic ethers.Nature chemistry · 2026Article
- Formally Stereoretentive SJournal of the American Chemical Society · 2025Article
- α-Halocarbonyls as a Valuable Functionalized Tertiary Alkyl Source.ChemistryOpen · 2024Review
- Rh-Catalyzed Enantioselective Single-Carbon Insertion of Alkenes.Journal of the American Chemical Society · 2024Article
- Deoxyfluorination of 1°, 2°, and 3° Alcohols by Nonbasic O-H Activation and Lewis Acid-Catalyzed Fluoride Shuttling.Journal of the American Chemical Society · 2023Article
- Highly Diastereoselective Preparation of Tertiary Alkyl Isonitriles by Stereoinvertive Nucleophilic Substitution at a Nonclassical Carbocation.Organic letters · 2023Article
- Stereoselective Construction of Tertiary Homoallyl Alcohols and Ethers by Nucleophilic Substitution at Quaternary Carbon Stereocenters.Angewandte Chemie (International ed. in English) · 2023Article
- Synthesis and Functionalization of Tertiary Propargylic Boronic Esters by Alkynyllithium-Mediated 1,2-Metalate Rearrangement of Borylated Cyclopropanes.Organic letters · 2022Article
- Modular Synthesis of α,α-Diaryl α-Amino Esters via Bi(V)-Mediated Arylation/SOrganic letters · 2022Article
- Borylated Cyclopropanes as Spring-Loaded Entities: Access to Vicinal Tertiary and Quaternary Carbon Stereocenters in Acyclic Systems.Journal of the American Chemical Society · 2022Article
- Stereoinvertive Nucleophilic Substitution at Quaternary Carbon Stereocenters of Cyclopropyl Ketones and Ethers.Angewandte Chemie (International ed. in English) · 2022Article
- Stereospecific Construction of Quaternary Carbon Stereocenters from Quaternary Carbon Stereocenters.Journal of the American Chemical Society · 2022Article
- Organocatalytic enantioselective SChemical science · 2021Article
- Benzyl thioether formation merging copper catalysis.RSC advances · 2021Article
- Enantiospecific deoxyfluorination of cyclic α-OH-β-ketoesters.Organic & biomolecular chemistry · 2021Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
2 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Nucleophilic substitution reactions have always been considered as one of the most powerful reactions for the creation of carbon-carbon or carbon-heteroatom bonds in organic synthesis. In contrast to secondary carbons, the steric shielding of tertiary carbons retards a concerted, stereospecific nucleophilic substitution, and ionizing pathways often lead to nonselective substitution due to ion pair dissociation. In this minireview, we will detail pioneering contributions and more recent achievements emphasizing the feasibility of nucleophilic substitution on tertiary stereocentres under certain conditions, with inversion of configuration. The development of these transformations at tertiary centres are of remarkable added value to practitioners in the field of complex molecule synthesis. A stereoselective substitution at a quaternary carbon stereocentre with inversion of configuration is also discussed in the case of a three-membered ring.
Identifiers
What OpenQuestion holds
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.