Evidence map›Paper›PMID 27454393›Full record

ArticleJournal of the American Chemical Society2016

Copper-Catalyzed Enantioselective Addition of Styrene-Derived Nucleophiles to Imines Enabled by Ligand-Controlled Chemoselective Hydrocupration.

Yang Yang, Ian B Perry, Stephen L Buchwald

Abstract read
In one paragraph

Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 42 papers.

0numbers the graph read from it
0cells of the map it votes in
42citing 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

42 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. Article
  5. Review
  6. Stereoselective Copper-Catalyzed Olefination of Imines.Angewandte Chemie (International ed. in English) · 2024
    Article
  7. Article
  8. Article
  9. Article
  10. Article
  11. A Diastereodivergent and Enantioselective Approach toJournal of the American Chemical Society · 2021
    Article
  12. Nickel-Catalyzed Annulations ofACS catalysis · 2021
    Article
  13. Article
  14. Enantioselective C(spNature chemistry · 2021
    Article
  15. Review
  16. Article
  17. Article
  18. Article
  19. Review
  20. 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

3 authors.

Yang YangDepartment of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Ian B PerryDepartment of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.
Stephen L BuchwaldDepartment of Chemistry, Massachusetts Institute of Technology , Cambridge, Massachusetts 02139, United States.

Funding

CATALYTIC METHODS FOR ORGANIC SYNTHESISR37GM046059 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BUCHWALD, STEPHEN L · 2000 to 2009
$8.1M
EARLY TRANSITION METAL CATALYSTS IN ORGANIC SYNTHESISR01GM046059 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BUCHWALD, STEPHEN L · 1992 to 2016
$5.4M
NIGMS NIH HHS R01 GM046059NIGMS NIH HHS R37 GM046059
6 · The paper itself

Abstract

The copper-catalyzed intermolecular enantioselective addition of styrenes to imines has been achieved under mild conditions at ambient temperature. This process features the use of styrenes as latent carbanion equivalents via the intermediacy of catalytically generated benzylcopper derivatives, providing an effective means for accessing highly enantiomerically enriched amines bearing contiguous stereocenters. Mechanistic studies shed light on the origin of the preferential styrene hydrocupration in the presence of an imine with the Ph-BPE-derived copper catalyst.

Indexed as

AminesCatalysisChemistry, PharmaceuticalCopperHydrocarbonsIminesLigandsMolecular StructureStereoisomerismStyreneStyrenesSubstrate SpecificityTemperatureAminesCopperHydrocarbonsIminesLigandsStyreneStyrenes

Identifiers

PMID27454393
PMCPMC5010012

What OpenQuestion holds

Textmetadata
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.