Evidence mapPaperPMID 41313757Full record

ArticleScience advances2025

Noncovalent interaction-driven regio- and enantioselective hydroalkynylation of unactivated alkenes to access remote chiral nitriles.

Fanling Meng, Xian He, Rui He, Guodong Ju, Genping Huang, Chao Wang

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Article in Science advances, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Not yet cited in PubMed.

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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.

2 · The registry

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3 · Its place in the literature

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4 · The record

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5 · Who and what money

Authors and funding

6 authors.

Fanling MengTianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, P. R. China.ORCID 0009-0008-4161-3221
Xian HeDepartment of Chemistry, School of Science, Tianjin University, Tianjin 300072, P. R. China.
Rui HeTianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, P. R. China.
Guodong JuTianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, P. R. China.ORCID 0009-0007-1744-7385
Genping HuangDepartment of Chemistry, School of Science, Tianjin University, Tianjin 300072, P. R. China.ORCID 0009-0006-6812-9398
Chao WangTianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin 300387, P. R. China.ORCID 0000-0001-6979-8506

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

Unactivated alkenes represent a challenging substrate for selective functionalization, particularly in achieving both regioselectivity and enantioselectivity. In this study, we present a strategy for the regio- and enantioselective hydroalkynylation of unactivated alkenes through the integration of noncovalent π⋯π interactions between the cyano group of the substrate and a chiral bis(oxazoline) ligand. The weak π⋯π interaction was supported by control experiments and computational studies. The method provides a reliable approach for synthesizing chiral nitriles with remote (β-, γ-, and δ-) stereocenters, which exhibit orthogonal reactivities and serve as valuable intermediates for further derivatization into otherwise difficult-to-access compounds. Our work provides a strategy for olefin functionalization and opens up avenues for the selective synthesis of chiral nitriles with remote stereocenters.

Identifiers

PMID41313757
PMCPMC12662212

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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 Socratic graph.