Evidence map›Paper›PMID 28294614›Full record

ArticleThe Journal of organic chemistry2017

Catalytic, Enantioselective, Intramolecular Sulfenoamination of Alkenes with Anilines.

Scott E Denmark, Hyung Min Chi

Abstract read
In one paragraph

Article in The Journal of organic chemistry, 2017. 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. Article
  3. Article
  4. Article
  5. Article
  6. Article
  7. Review
  8. Article
  9. Article
  10. Article
  11. Article
  12. (Organic syntheses; an annual publication of satisfactory methods for the preparation of organic chemicals · 2019
    Article
  13. Enantioselective, Lewis Base-Catalyzed Sulfenocyclization of Polyenes.Journal of the American Chemical Society · 2018
    Article
  14. Article
  15. Article
  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

2 authors.

Scott E DenmarkRoger Adams Laboratory, Department of Chemistry, University of Illinois , Urbana, Illinois 61801, United States.ORCID 0000-0002-1099-9765
Hyung Min ChiRoger Adams Laboratory, Department of Chemistry, University of Illinois , Urbana, Illinois 61801, United States.

Funding

Organosilicon-Based Cross-Coupling ReactionsR01GM063167 · NIGMS · UNIVERSITY OF ILLINOIS URBANA-CHAMPAIGN · PI DENMARK, SCOTT ERIC · 2002 to 2009
$2.5M
Asymmetric Lewis Base Catalysis in Main Group ChemistryR01GM085235 · NIGMS · UNIVERSITY OF ILLINOIS AT URBANA-CHAMPAIGN · PI DENMARK, SCOTT ERIC · 2010 to 2017
$2.4M
THE CYCLOADDITION CHEMISTRY OF NITROALKENESR01GM030938 · NIGMS · UNIVERSITY OF ILLINOIS URBANA-CHAMPAIGN · PI DENMARK, SCOTT ERIC · 1985 to 2007
$2.1M
NIGMS NIH HHS R01 GM030938NIGMS NIH HHS R01 GM063167NIGMS NIH HHS R01 GM085235
6 · The paper itself

Abstract

A method for the catalytic, enantioselective, intramolecular sulfenoamination of alkenes with aniline nucleophiles has been developed. The method employs a chiral, Lewis basic selenophosphoramide catalyst and a Brønsted acid co-catalyst to promote stereocontrolled C-N and C-S bond formation by activation of an achiral sulfenylating agent. Benzoannulated nitrogen-containing heterocycles such as indolines, tetrahydroquinolines, and tetrahydrobenzazepines were prepared with high to excellent enantioselectivities. The impact of tether length and electron density of both the nucleophile and olefin on the reactivity, site selectivity, and enantioselectivity were investigated and interpreted in terms of substrate-dependent stereodetermining thiiranium ion formation or capture.

Indexed as

AlkenesAminationAniline CompoundsCatalysisLewis BasesStereoisomerismAlkenesAniline CompoundsLewis Bases

Identifiers

PMID28294614
PMCPMC5388071

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.