ArticleJournal of the American Chemical Society2019
Disodium Salts of Pseudoephedrine-Derived Myers Enolates: Stereoselectivity and Mechanism of Alkylation.
Article in Journal of the American Chemical Society, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 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
9 citing papers in PubMed, 21 citations in OpenAlex.
- Surface tailoring of porphyrinRSC advances · 2025Article
- Copper(I)-Catalyzed Enantioselective α-Alkylation of 2-Acylimidazoles.Journal of the American Chemical Society · 2024Article
- Copper(I)-catalyzed asymmetric alkylation of α-imino-esters.Nature communications · 2023Article
- Lithiated Oppolzer Enolates: Solution Structures, Mechanism of Alkylation, and Origin of Stereoselectivity.Journal of the American Chemical Society · 2022Article
- Sodium Isopropyl(trimethylsilyl)amide: A Stable and Highly Soluble Lithium Diisopropylamide Mimic.The Journal of organic chemistry · 2022Article
- Catalytic Enantioselective α-Alkylation of Amides by Unactivated Alkyl Electrophiles.Journal of the American Chemical Society · 2022Article
- Continuous Flow Preparation of Benzylic Sodium Organometallics.Angewandte Chemie (International ed. in English) · 2022Article
- (2-Ethylhexyl)sodium: A Hexane-Soluble Reagent for Br/Na-Exchanges and Directed Metalations in Continuous Flow.Angewandte Chemie (International ed. in English) · 2021Article
- Article
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Pseudoephedrine-derived dianionic Myers enolates were generated using sodium diisopropylamide (NaDA) in THF solution. The reactivities and selectivities of the disodium salts largely mirror those of the dilithium salts but without the requisite large excesses of inorganic salts (LiCl) or mandated dilute solutions. The disodium salts require careful control of temperature to preclude deleterious aggregate aging effects traced to changes in the aggregate structure and intervening O-alkylations. Structural studies and density functional theory (DFT) computations show a dominant highly symmetric polyhedron quite different from the lithium analogue. No enolate-NaDA mixed aggregates are observed with excess NaDA. Rate studies show an alkylation mechanism involving an intervening tetramer-monomer pre-equilibrium followed by rate-limiting alkylation of tetrasolvated monomers. DFT computations were conducted to explore the possible influences on stereochemistry. A crystal deriving from samples aged at ambient temperature contains six dianionic subunits and two monoanionic (alkoxide-only) subunits. A new preparation of concentrated solutions of NaDA in THF solution is described.
Indexed as
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.