Evidence map›Paper›PMID 38860250›Full record

ArticleRSC advances2024

N-heterocyclic carbene catalyzed [2 + 3] annulation reaction for the synthesis of trifluoroethyl 3,2'-spirooxindole γ-lactam.

Yiru Pu, Maolin Wang, Wanrong Tian, Xian Ge, Dikai Zhu, Chuanqi Wang, Yingjie Zeng, Feiyan Tao, Yun Deng, Jun Lu

Abstract read
In one paragraph

Article in RSC advances, 2024. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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

0 citing papers in PubMed.

No citing paper in PubMed yet.

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

10 authors.

Yiru PuState Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine Chengdu 611137 China dengyun2000@hotmail.com ljaaa111@163.com.
Maolin WangClinical Research Center, The First Affiliated Hospital of Shantou University Medical College Shantou Guangdong Province 515000 China.
Wanrong TianState Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine Chengdu 611137 China dengyun2000@hotmail.com ljaaa111@163.com.
Xian GeState Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine Chengdu 611137 China dengyun2000@hotmail.com ljaaa111@163.com.
Dikai ZhuResearch and Development Centre, China Tobacco Sichuan Industrial Co. Ltd Chengdu 610066 China taofeiyan@163.com.
Chuanqi WangState Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine Chengdu 611137 China dengyun2000@hotmail.com ljaaa111@163.com.
Yingjie ZengState Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine Chengdu 611137 China dengyun2000@hotmail.com ljaaa111@163.com.
Feiyan TaoResearch and Development Centre, China Tobacco Sichuan Industrial Co. Ltd Chengdu 610066 China taofeiyan@163.com.
Yun DengState Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine Chengdu 611137 China dengyun2000@hotmail.com ljaaa111@163.com.
Jun LuState Key Laboratory of Southwestern Chinese Medicine Resources, School of Pharmacy, Chengdu University of Traditional Chinese Medicine Chengdu 611137 China dengyun2000@hotmail.com ljaaa111@163.com.ORCID https://orcid.org/0000-0003-1625-8682

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Asymmetric catalytic processes promoted by N-heterocyclic carbenes (NHCs) hold great potential for the sustainable preparation of chiral molecules. However, catalyzing the reactions by manipulating the reactive intermediates is challenging. We report herein that the known NHC-catalyzed [3 + 2] annulation reaction between ketimine and enal can also be turned into a [2 + 3] annulation reaction for the highly enantioselective direct synthesis of trifluoroethyl 3,2'-spirooxindole γ-lactams (4) through timely catalysis of the intermediates. DFT calculations revealed that this transformation included the key step of the nucleophilic attack of the Breslow intermediate M2 derived from NHC and enal (2) to the unattacked ketimine (1). Our study demonstrates that it is possible to tune the desired selectivities through the dynamic catalysts of the reactive intermediates.

Identifiers

PMID38860250
PMCPMC11163332

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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.