Evidence map›Paper›PMID 31099584›Full record

ArticleOrganic letters2019

Regio- and Enantioselective Synthesis of 1,2-Diamine Derivatives by Copper-Catalyzed Hydroamination.

Saki Ichikawa, Xi-Jie Dai, Stephen L Buchwald

Abstract read
In one paragraph

Article in Organic letters, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 5 papers.

0numbers the graph read from it
0cells of the map it votes in
5citing 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

5 citing papers in PubMed.

  1. Iridium-catalysed hydroamination of internal homoallylic amines.Chemical communications (Cambridge, England) · 2024
    Article
  2. Electrophilic Aminating Agents in Total Synthesis.Angewandte Chemie (International ed. in English) · 2021
    Review
  3. Article
  4. Distinctive reactivity ofBeilstein journal of organic chemistry · 2020
    Article
  5. 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.

Saki IchikawaDepartment of Chemistry , Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , United States.ORCID 0000-0002-6764-2273
Xi-Jie DaiDepartment of Chemistry , Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , United States.ORCID 0000-0002-4899-6359
Stephen L BuchwaldDepartment of Chemistry , Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , United States.ORCID 0000-0003-3875-4775

Funding

Metal-Catalyzed Methods for Organic SynthesisR35GM122483 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI STEPHEN L BUCHWALD · 2017 to 2026
$11.4M
LATE TRANSITION METAL CATALYSTS FOR ORGANIC SYNTHESISR01GM058160 · NIGMS · MASSACHUSETTS INSTITUTE OF TECHNOLOGY · PI BUCHWALD, STEPHEN L · 1998 to 2016
$9.0M
NIGMS NIH HHS R01 GM058160NIGMS NIH HHS R35 GM122483
6 · The paper itself

Abstract

A highly regio- and enantioselective synthesis of 1,2-diamine derivatives from γ-substituted allylic pivalamides using copper-catalyzed hydroamination is reported. The N-pivaloyl group is essential, in both facilitating the hydrocupration step and suppressing an unproductive β-elimination from the alkylcopper intermediate. This approach enables an efficient construction of chiral differentially protected vicinal diamines under mild conditions with broad functional group tolerance.

Indexed as

AminationCatalysisCopperDiaminesMolecular StructureStereoisomerismCopperDiamines

Identifiers

PMID31099584
PMCPMC6825330

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.