Conversion of anilines to chiral benzylic amines via formal one-carbon insertion into aromatic C-N bonds.

Lei Li, Min Yang, Qiuqin He, Renhua Fan

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Article in Nature communications, 2020. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it

0cells of the map it votes in

2citing papers in PubMed

1.5field-weighted citation impact, top 19% of its field

1 · What the graph read from it

What it found

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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.

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3 · Its place in the literature

Who cites it

2 citing papers in PubMed, 25 citations in OpenAlex.

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Article

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5 · Who and what money

Authors and funding

4 authors at 2 institutions in 1 country.

Lei LiDepartment of Chemistry, Fudan University, 200433, Shanghai, China.

Min YangDepartment of Forensic Science, Oil-tea in Medical Health Care and Functional Product Development Engineering Research Center in Jiangxi, Gannan Medical University, Ganzhou, 341000, China.

Qiuqin HeDepartment of Chemistry, Fudan University, 200433, Shanghai, China.

Renhua FanDepartment of Chemistry, Fudan University, 200433, Shanghai, China. rhfan@fudan.edu.cn.ORCID http://orcid.org/0000-0001-7398-3368

Fudan University · CNGannan Medical University · CN

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Insertion of atoms into aromatic carbon-nitrogen bonds is an appealing method for the synthesis of nitrogen-containing molecules and it has the advantage of the availability and abundance of anilines. However, the direct cleavage of aromatic carbon-nitrogen bonds is challenging due to the particularly inert and stable nature of these bonds. Here we report a formal, enantioselective one-carbon insertion into an aromatic carbon-nitrogen bond via an aromaticity dissembly-reconstruction process to directly convert anilines to chiral α-branched benzylic amines. The process involves oxidative dearomatization of para-substituted anilines, chiral sulfur ylide-mediated asymmetric aziridination, and subsequent rearrangement. Chiral sulfur ylides serve as one-carbon insertion units.

Identifiers

PMID32968063

DOI10.1021/ja9100276

PMCPMC7511326

OpenAlexW3088366388

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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.