Evidence map›Paper›PMID 32648755›Full record

ArticleThe Journal of organic chemistry2020

Mechanistic Studies of the TRIP-Catalyzed Allylation with Organozinc Reagents.

Peter E Hartmann, Mattia Lazzarotto, Jakob Pletz, Stefan Tanda, Philipp Neu, Walter Goessler, Wolfgang Kroutil, A Daniel Boese, Michael Fuchs

Open access · hybridAbstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in The Journal of organic chemistry, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing papers in PubMed
0.4field-weighted citation impact, top 44% of its field
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

1 citing paper in PubMed, 7 citations in OpenAlex.

  1. 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

9 authors at 1 institution in 1 country.

Peter E HartmannBioorganic and Organic Chemistry, Institute of Chemistry, University of Graz, Heinrichstrasse 28/II, 8010 Graz, Austria, Europe.
Mattia LazzarottoBioorganic and Organic Chemistry, Institute of Chemistry, University of Graz, Heinrichstrasse 28/II, 8010 Graz, Austria, Europe.
Jakob PletzBioorganic and Organic Chemistry, Institute of Chemistry, University of Graz, Heinrichstrasse 28/II, 8010 Graz, Austria, Europe.
Stefan TandaAnalytical Chemistry, Institute of Chemistry, University of Graz, Universitätsplatz 1/I, 8010 Graz, Austria, Europe.ORCID 0000-0001-8654-4057
Philipp NeuBioorganic and Organic Chemistry, Institute of Chemistry, University of Graz, Heinrichstrasse 28/II, 8010 Graz, Austria, Europe.
Walter GoesslerAnalytical Chemistry, Institute of Chemistry, University of Graz, Universitätsplatz 1/I, 8010 Graz, Austria, Europe.
Wolfgang KroutilBioorganic and Organic Chemistry, Institute of Chemistry, University of Graz, Heinrichstrasse 28/II, 8010 Graz, Austria, Europe.ORCID 0000-0002-2151-6394
A Daniel BoesePhysical and Theoretical Chemistry, Institute of Chemistry, University of Graz, Heinrichstrasse 28/IV, 8010 Graz, Austria, Europe.ORCID 0000-0001-7388-778X
Michael FuchsBioorganic and Organic Chemistry, Institute of Chemistry, University of Graz, Heinrichstrasse 28/II, 8010 Graz, Austria, Europe.ORCID 0000-0001-6757-7638
University of Graz · AT

Funding

Austrian Science Fund FWF P 31276
6 · The paper itself

Abstract

3,3-Bis(2,4,6-triisopropylphenyl)-1,1-binaphthyl-2,2-diyl hydrogenphosphate (TRIP) catalyzes the asymmetric allylation of aldehydes with organozinc compounds, leading to highly valuable structural motifs, like precursors to lignan natural products. Our previously reported mechanistic proposal relies on two reaction intermediates and requires further investigation to really understand the mode of action and the origins of stereoselectivity. Detailed ab initio calculations, supported by experimental data, render a substantially different mode of action to the allyl boronate congener. Instead of a Brønsted acid-based catalytic activation, the chiral phosphate acts as a counterion for the Lewis acidic zinc ion, which provides the activation of the aldehyde.

Identifiers

PMID32648755
PMCPMC7418105
OpenAlexW3041552607

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.