Evidence map›Paper›PMID 36435942›Full record

ArticleNature communications2022

Chiral aldehyde-nickel dual catalysis enables asymmetric α-propargylation of amino acids and stereodivergent synthesis of NP25302.

Fang Zhu, Chao-Xing Li, Zhu-Lian Wu, Tian Cai, Wei Wen, Qi-Xiang Guo

Abstract read
In one paragraph

Article in Nature communications, 2022. 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. Review
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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

6 authors.

Fang ZhuKey Laboratory of Applied Chemistry of Chongqing Municipality, and Chongqing Key Laboratory of Soft-Matter Material Chemistry and Function Manufacturing, School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China.
Chao-Xing LiKey Laboratory of Applied Chemistry of Chongqing Municipality, and Chongqing Key Laboratory of Soft-Matter Material Chemistry and Function Manufacturing, School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China.
Zhu-Lian WuKey Laboratory of Applied Chemistry of Chongqing Municipality, and Chongqing Key Laboratory of Soft-Matter Material Chemistry and Function Manufacturing, School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China.ORCID 0000-0001-8444-4028
Tian CaiKey Laboratory of Applied Chemistry of Chongqing Municipality, and Chongqing Key Laboratory of Soft-Matter Material Chemistry and Function Manufacturing, School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China.ORCID 0000-0003-3288-4288
Wei WenKey Laboratory of Applied Chemistry of Chongqing Municipality, and Chongqing Key Laboratory of Soft-Matter Material Chemistry and Function Manufacturing, School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China. wenwei1989@swu.edu.cn.ORCID 0000-0001-5100-8545
Qi-Xiang GuoKey Laboratory of Applied Chemistry of Chongqing Municipality, and Chongqing Key Laboratory of Soft-Matter Material Chemistry and Function Manufacturing, School of Chemistry and Chemical Engineering, Southwest University, Chongqing, 400715, China. qxguo@swu.edu.cn.ORCID 0000-0002-0405-7958

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

The combined catalytic systems derived from organocatalysts and transition metals exhibit powerful activation and stereoselective-control abilities in asymmetric catalysis. This work describes a highly efficient chiral aldehyde-nickel dual catalytic system and its application for the direct asymmetric α-propargylation reaction of amino acid esters with propargylic alcohol derivatives. Various structural diversity α,α-disubstituted non-proteinogenic α-amino acid esters are produced in good-to-excellent yields and enantioselectivities. Furthermore, a stereodivergent synthesis of natural product NP25302 is achieved, and a reasonable reaction mechanism is proposed to illustrate the observed stereoselectivity based on the results of control experiments, nonlinear effect investigation, and HRMS detection.

Indexed as

AldehydesAmino AcidsCatalysisEstersNickelPyrrolizidine AlkaloidsStereoisomerismAldehydesAmino AcidsEstersNickelNP 25302Pyrrolizidine Alkaloids

Identifiers

PMID36435942
PMCPMC9701212

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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.