ArticleNature communications2019
Stereoselective synthesis of medium lactams enabled by metal-free hydroalkoxylation/stereospecific [1,3]-rearrangement.
Article in Nature communications, 2019. 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.
- Organocatalytic C─O Bond Cleavage and Asymmetric Transformations via [1,3]-Sigmatropic Rearrangement.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Article
- Synthesis and Enzymatic Evaluation of a Small Library of Substituted Phenylsulfonamido-Alkyl Sulfamates towards Carbonic Anhydrase II.Molecules (Basel, Switzerland) · 2024Article
- Enantioselective functionalization of unactivated C(spNature communications · 2024Article
- Organocatalytic intramolecular (4 + 2) annulation of enals with ynamides: atroposelective synthesis of axially chiral 7-aryl indolines.Chemical science · 2023Article
- Atom-economic and stereoselective catalytic synthesis of fully substituted enol esters/carbonates of amides in acyclic systems enabled by boron Lewis acid catalysis.Chemical science · 2023Article
- Modular enantioselective access to β-amino amides by Brønsted acid-catalysed multicomponent reactions.Nature chemistry · 2023Article
- Boron Lewis Acid Catalysis Enables the Direct Cyanation of Benzyl Alcohols by Means of Isonitrile as Cyanide Source.Molecules (Basel, Switzerland) · 2023Article
- Triflamides and Triflimides: Synthesis and Applications.Molecules (Basel, Switzerland) · 2022Review
- Asymmetric dearomatization catalysed by chiral Brønsted acids via activation of ynamides.Nature chemistry · 2021Article
- Access to Indole-Annulated Medium-Sized Lactams through Protonation/Deuteration-Induced Ring-Opening of Spiroindolines.ACS omega · 2021Article
- Copper-catalyzed asymmetric cyclization of alkenyl diynes: method development and new mechanistic insights.Chemical science · 2021Article
- A Synthetic Strategy toward Eight-Membered Cyclic Amines by Cycloetherification and Claisen Rearrangement.Organic letters · 2021Article
- Asymmetric synthesis with ynamides: unique reaction control, chemical diversity and applications.Chemical Society reviews · 2020Article
- Chiral Fe(ii) complex catalyzed enantioselective [1,3] O-to-C rearrangement of alkyl vinyl ethers and synthesis of chromanols and beyond.Chemical science · 2020Article
- A happy medium: the synthesis of medicinally important medium-sized ringsChemical science · 2020Review
Corrections and comments
PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.
Authors and funding
10 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Rearrangement reactions have attracted considerable interest over the past decades due to their high bond-forming efficiency and atom economy in the construction of complex organic architectures. In contrast to the well-established [3,3]-rearrangement, [1,3] O-to-C rearrangement has been far less vigorously investigated, and stereospecific [1,3]-rearrangement is extremely rare. Here, we report a metal-free intramolecular hydroalkoxylation/[1,3]-rearrangement, leading to the practical and atom-economical assembly of various valuable medium-sized lactams with wide substrate scope and excellent diastereoselectivity. Moreover, such an asymmetric cascade cyclization has also been realized by chiral Brønsted acid-catalyzed kinetic resolution. In addition, biological tests reveal that some of these medium-sized lactams displayed their bioactivity as antitumor agents against melanoma cells, esophageal cancer cells and breast cancer cells. A mechanistic rationale for the reaction is further supported by control experiments and theoretical calculations.
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.