Evidence map›Paper›PMID 33464093›Full record

ArticleOrganic letters2021

α-C-H Bond Functionalization of Unprotected Alicyclic Amines: Lewis-Acid-Promoted Addition of Enolates to Transient Imines.

Jae Hyun Kim, Anirudra Paul, Ion Ghiviriga, Daniel Seidel

Open access · greenAbstract read
In one paragraph

Article in Organic letters, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.

0numbers the graph read from it
0cells of the map it votes in
13citing papers in PubMed
1.7field-weighted citation impact, top 17% of its field
1 · What the graph read from it

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.

2 · The registry

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.

3 · Its place in the literature

Who cites it

13 citing papers in PubMed, 21 citations in OpenAlex.

  1. Deciphering competing reaction pathways in the α-C-H functionalization of unprotected alicyclic aminesOrganic chemistry frontiers : an international journal of organic chemistry · 2026
    Article
  2. Review
  3. Cyclic Imine-BFSynlett : accounts and rapid communications in synthetic organic chemistry · 2025
    Article
  4. Photocatalytic Decarboxylative Alkylation of Cyclic Imine-BFJournal of the American Chemical Society · 2024
    Article
  5. Article
  6. Alicyclic-Amine-Derived Imine-BFAngewandte Chemie (International ed. in English) · 2024
    Article
  7. Article
  8. Article
  9. Review
  10. Article
  11. Article
  12. Article
  13. Article
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

4 authors at 1 institution in 1 country.

Jae Hyun KimCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.
Anirudra PaulCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.
Ion GhivirigaCenter for NMR Spectroscopy, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.ORCID http://orcid.org/0000-0001-5812-5170
Daniel SeidelCenter for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, Florida 32611, United States.ORCID http://orcid.org/0000-0001-6725-111X
University of Florida · US

Funding

Development of Strategies for the Functionalization of AminesR01GM101389 · NIGMS · UNIVERSITY OF FLORIDA · PI SEIDEL, DANIEL · 2012 to 2021
$2.5M
Acquisition of a Q Exactive HF Hybrid Quadrupole-OrbitrapS10OD021758 · OD · UNIVERSITY OF FLORIDA · PI BASSO, KARI B · 2017 to 2017
$600k
NIGMS NIH HHS R01 GM101389NIH HHS S10 OD021758
6 · The paper itself

Abstract

Enolizable cyclic imines, obtained in situ from their corresponding lithium amides by oxidation with simple ketone oxidants, are readily alkylated with a range of enolates to provide mono- and polycyclic β-aminoketones in a single operation, including the natural product (±)-myrtine. Nitrile anions also serve as competent nucleophiles in these transformations, which are promoted by BF

Identifiers

PMID33464093
PMCPMC7924990
OpenAlexW3123655061

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

Registered trials

None linked

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.