A DFT calculation-inspired Rh(i)-catalyzed reaction

Shunying Liu, Jun Jiang, Jianghui Chen, Qinghua Wei, Wenfeng Yao, Fei Xia, Wenhao Hu

Open access · diamondAbstract read

In one paragraph

Article in Chemical science, 2017. 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

1.7field-weighted citation impact, top 17% 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

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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, 34 citations in OpenAlex.

Rh(I)/Sc(OTf)Molecular diversity · 2019
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

7 authors at 3 institutions in 1 country.

Shunying LiuShanghai Engineering Research Center of Molecular Therapeutics and New Drug Development , East China Normal University , Shanghai , 200062 , China . Email: fxia@chem.ecnu.edu.cn ; Email: whu@chem.ecnu.edu.cn.ORCID 0000-0002-3894-757X

Jun JiangSchool of Chemistry and Chemical Engineering , Guangxi University , Nanning , 530004 , China.

Jianghui ChenShanghai Engineering Research Center of Molecular Therapeutics and New Drug Development , East China Normal University , Shanghai , 200062 , China . Email: fxia@chem.ecnu.edu.cn ; Email: whu@chem.ecnu.edu.cn.

Qinghua WeiShanghai Engineering Research Center of Molecular Therapeutics and New Drug Development , East China Normal University , Shanghai , 200062 , China . Email: fxia@chem.ecnu.edu.cn ; Email: whu@chem.ecnu.edu.cn.

Wenfeng YaoShanghai Engineering Research Center of Molecular Therapeutics and New Drug Development , East China Normal University , Shanghai , 200062 , China . Email: fxia@chem.ecnu.edu.cn ; Email: whu@chem.ecnu.edu.cn.

Fei XiaShanghai Engineering Research Center of Molecular Therapeutics and New Drug Development , East China Normal University , Shanghai , 200062 , China . Email: fxia@chem.ecnu.edu.cn ; Email: whu@chem.ecnu.edu.cn.ORCID 0000-0001-9458-9175

Wenhao HuShanghai Engineering Research Center of Molecular Therapeutics and New Drug Development , East China Normal University , Shanghai , 200062 , China . Email: fxia@chem.ecnu.edu.cn ; Email: whu@chem.ecnu.edu.cn.ORCID 0000-0003-1511-2614

East China Normal University · CNGuangxi University · CNNew York University Shanghai · CN

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Metal-associated carbenes from diazo compounds promote many useful chemistry transformations in modern organic chemistry. However, compared to α-aryldiazoacetate-derived carbenes (ArDCs), the synthetic application of α-alkyldiazoacetate-derived carbenes (AlDCs) is greatly limited due to intramolecular α-H transfer (elimination) that results in alkenes as the main by-products. An intriguing α-alkyldiazoacetate-involved three-component reaction has been developed following DFT calculation inspiration to provide β-hydroxyl α-alkyl-α-amino acid derivatives in good yields. The intramolecular α-H shift of an α-alkyldiazoacetate-derived carbene was successfully suppressed by the association of a Rh(i) complex to form the corresponding active ammonium ylide, which was trapped before the fast 1,2-H transfer process. A Rh(i)-chiral diene complex was identified as an effective catalyst to give an asymmetric version of the reaction with good enantioselectivity. This reaction provides insight into extending the efficient transformation of α-alkyldiazoacetate-derived carbenes and their synthetic application.

Identifiers

PMID29081965

DOI10.1039/c7sc00257b

PMCPMC5635810

OpenAlexW2600397526

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LicenceCC BY

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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.