Organocatalytic intramolecular (4 + 2) annulation of enals with ynamides: atroposelective synthesis of axially chiral 7-aryl indolines.

Zhi-Xin Zhang, Li-Gao Liu, Yi-Xi Liu, Jian Lin, Xin Lu, Long-Wu Ye, Bo Zhou

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Article in Chemical science, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 3 papers.

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3citing papers in PubMed

2.5field-weighted citation impact, top 11% of its field

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3 citing papers in PubMed, 17 citations in OpenAlex.

Organocatalytic enantioselective synthesis of double S-shaped quadruple helicene-like molecules.Nature communications · 2025
Article
Recent advances in organocatalytic atroposelective reactions.Beilstein journal of organic chemistry · 2025
Review
Synthesis and Enzymatic Evaluation of a Small Library of Substituted Phenylsulfonamido-Alkyl Sulfamates towards Carbonic Anhydrase II.Molecules (Basel, Switzerland) · 2024
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7 authors at 1 institution in 1 country.

Zhi-Xin ZhangState Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University Xiamen 361005 China zhoubo@xmu.edu.cn xinlu@xmu.edu.cn.

Li-Gao LiuState Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University Xiamen 361005 China zhoubo@xmu.edu.cn xinlu@xmu.edu.cn.

Yi-Xi LiuState Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University Xiamen 361005 China zhoubo@xmu.edu.cn xinlu@xmu.edu.cn.

Jian LinState Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University Xiamen 361005 China zhoubo@xmu.edu.cn xinlu@xmu.edu.cn.

Xin LuState Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University Xiamen 361005 China zhoubo@xmu.edu.cn xinlu@xmu.edu.cn.ORCID https://orcid.org/0000-0003-4968-9462

Long-Wu YeState Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University Xiamen 361005 China zhoubo@xmu.edu.cn xinlu@xmu.edu.cn.ORCID https://orcid.org/0000-0003-3108-2611

Bo ZhouState Key Laboratory of Physical Chemistry of Solid Surfaces, Key Laboratory of Chemical Biology of Fujian Province, College of Chemistry and Chemical Engineering, Xiamen University Xiamen 361005 China zhoubo@xmu.edu.cn xinlu@xmu.edu.cn.ORCID https://orcid.org/0000-0002-5551-678X

Xiamen University · CN

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6 · The paper itself

Abstract

Catalytic enantioselective transformation of alkynes has become a powerful tool for the synthesis of axially chiral molecules. Most of these atroposelective reactions of alkynes rely on transition-metal catalysis, and the organocatalytic approaches are largely limited to special alkynes which act as the precursors of Michael acceptors. Herein, we disclose an organocatalytic atroposelective intramolecular (4 + 2) annulation of enals with ynamides. This method allows the efficient and highly atom-economical preparation of various axially chiral 7-aryl indolines in generally moderate to good yields with good to excellent enantioselectivities. Computational studies were carried out to elucidate the origins of regioselectivity and enantioselectivity. Furthermore, a chiral phosphine ligand derived from the synthesized axially chiral 7-aryl indoline was proven to be potentially applicable to asymmetric catalysis.

Identifiers

PMID37293635

DOI10.1039/d3sc01880f

PMCPMC10246658

OpenAlexW4376861892

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