Evidence map›Paper›PMID 25940066›Full record

ArticleOrganic & biomolecular chemistry2015

Tandem rhodium catalysis: exploiting sulfoxides for asymmetric transition-metal catalysis.

K G M Kou, V M Dong

Abstract read
In one paragraph

Article in Organic & biomolecular chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.

0numbers the graph read from it
0cells of the map it votes in
4citing 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

4 citing papers in PubMed.

  1. Article
  2. Article
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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.

K G M KouDepartment of Chemistry, University of California, Irvine, CA 92697, USA. dongv@uci.edu.
V M Dong

Funding

Catalytic hydroacylation: Transforming C-H bonds into biorelevant esters and ketonesR01GM105938 · NIGMS · UNIVERSITY OF CALIFORNIA-IRVINE · PI DONG, VY M · 2013 to 2017
$1.3M
NIGMS NIH HHS GM105938NIGMS NIH HHS R01 GM105938
6 · The paper itself

Abstract

Sulfoxides are uncommon substrates for transition-metal catalysis due to their propensity to inhibit catalyst turnover. In a collaborative effort with Ken Houk, we developed the first dynamic kinetic resolution (DKR) of allylic sulfoxides using asymmetric rhodium-catalyzed hydrogenation. A detailed mechanistic analysis of this transformation using both experimental and theoretical methods revealed rhodium to be a tandem catalyst that promoted both hydrogenation of the alkene and racemization of the allylic sulfoxide. Using a combination of deuterium labelling and DFT studies, a novel mode of allylic sulfoxide racemization via a Rh(III)-π-allyl intermediate was identified.

Indexed as

AlkenesAllyl CompoundsCatalysisHydrogenationKineticsRhodiumStereoisomerismSulfoxidesAlkenesAllyl CompoundsRhodiumSulfoxides

Identifiers

PMID25940066
PMCPMC4455901

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.