Evidence map›Paper›PMID 27094932›Full record

ArticleAngewandte Chemie (International ed. in English)2016

Enantioselective, Stereodivergent Hydroazidation and Hydroamination of Allenes Catalyzed by Acyclic Diaminocarbene (ADC) Gold(I) Complexes.

Dimitri A Khrakovsky, Chuanzhou Tao, Miles W Johnson, Richard T Thornbury, Sophia L Shevick, F Dean Toste

Abstract read
In one paragraph

Article in Angewandte Chemie (International ed. in English), 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.

0numbers the graph read from it
0cells of the map it votes in
14citing 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

14 citing papers in PubMed.

  1. Article
  2. Article
  3. Article
  4. AuInternational journal of molecular sciences · 2025
    Article
  5. Article
  6. Article
  7. Synthetically Versatile Nitrogen Acyclic Carbene Stabilized Gold Nanoparticles.Chemistry (Weinheim an der Bergstrasse, Germany) · 2020
    Article
  8. Article
  9. Review
  10. Article
  11. Article
  12. Article
  13. Article
  14. On the Winstein rearrangement: equilibrium and mechanism.ARKIVOC : free online journal of organic chemistry
    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

6 authors.

Dimitri A KhrakovskyDepartment of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.
Chuanzhou TaoDepartment of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.
Miles W JohnsonDepartment of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.
Richard T ThornburyDepartment of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.
Sophia L ShevickDepartment of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA.
F Dean TosteDepartment of Chemistry, University of California, Berkeley, Berkeley, CA, 94720, USA. fdtoste@berkeley.edu.

Funding

Catalytic Methods for Carbon-Carbon Bond FormationR01GM073932 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI TOSTE, F. DEAN · 2005 to 2014
$2.5M
New Transition Metal Catalysts for Organic ReactionsR01GM074774 · NIGMS · UNIVERSITY OF CALIFORNIA BERKELEY · PI TOSTE, F. DEAN · 2007 to 2010
$1.2M
A proposal for the purchase of a new Cu anode Microsource X-ray Diffractometer wiS10RR027172 · NCRR · UNIVERSITY OF CALIFORNIA BERKELEY · PI RAYMOND, KENNETH N · 2010 to 2010
$500k
NCRR NIH HHS S10 RR027172NIGMS NIH HHS R01 GM073932NIGMS NIH HHS R01 GM074774
6 · The paper itself

Abstract

The gold-catalyzed enantioselective hydroazidation and hydroamination reactions of allenes are presented herein. ADC gold(I) catalysts derived from BINAM were critical for achieving high levels of enantioselectivity in both transformations. The sense of enantioinduction is reversed for the two different nucleophiles, allowing access to both enantiomers of the corresponding allylic amines using the same catalyst enantiomer.

Indexed as

AlkadienesAminesCatalysisCoordination ComplexesGoldMethaneStereoisomerismAlkadienesAminescarbeneCoordination ComplexesGoldMethaneacyclic diaminocarbeneenantioselective synthesisgold catalysishydroaminationhydroazidation

Identifiers

PMID27094932
PMCPMC4948301

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.