Evidence map›Paper›PMID 24604837›Full record

ArticleAngewandte Chemie (International ed. in English)2014

Regio- and stereoselective 1,2-dihydropyridine alkylation/addition sequence for the synthesis of piperidines with quaternary centers.

Simon Duttwyler, Shuming Chen, Colin Lu, Brandon Q Mercado, Robert G Bergman, Jonathan A Ellman

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.

0numbers the graph read from it
0cells of the map it votes in
16citing papers in PubMed
–field-weighted citation impact
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

16 citing papers in PubMed.

  1. Article
  2. Substituted Dihydropyridine Synthesis by Dearomatization of Pyridines.Angewandte Chemie (International ed. in English) · 2021
    Article
  3. Review
  4. Article
  5. Review
  6. Article
  7. Article
  8. Article
  9. Article
  10. Article
  11. Article
  12. Article
  13. Rh(I)-Catalyzed Cycloisomerization of 1,6-Enynes.Synlett : accounts and rapid communications in synthetic organic chemistry · 2015
    Article
  14. Article
  15. Review
  16. Review
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

6 authors.

Simon DuttwylerDepartment of Chemistry, Yale University, 225 Prospect St., New Haven, CT 06520 (USA).
Shuming Chen
Colin Lu
Brandon Q Mercado
Robert G Bergman
Jonathan A Ellman

Funding

C-H Functionalization for the Synthesis of Amines and Nitrogen HeterocyclesR01GM069559 · NIGMS · YALE UNIVERSITY · PI ELLMAN, JONATHAN A · 2004 to 2017
$5.4M
NIGMS NIH HHS GM069559NIGMS NIH HHS R01 GM069559
6 · The paper itself

Abstract

The first example of C alkylation of 1,2-dihydropyridines with alkyl triflates and Michael acceptors was developed to introduce quaternary carbon centers with high regio- and diastereoselectivity. Hydride or carbon nucleophile addition to the resultant iminium ion also proceeded with high diastereoselectivity. Carbon nucleophile addition results in an unprecedented level of substitution to provide piperidine rings with adjacent tetrasubstituted carbon atoms.

Indexed as

AlkylationCatalysisDihydropyridinesMolecular StructurePiperidinesStereoisomerismDihydropyridinespiperidinePiperidinesalkylationdiastereoselectivityheterocyclesreductionsynthetic methods

Identifiers

PMID24604837
PMCPMC4058641

What OpenQuestion holds

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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.