通过级联 1,6-加成/环化/非选择性质子化途径有机催化不对称合成磺酰基取代的呋喃

IF 13.1 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2024-08-08 DOI:10.1021/acscatal.4c03027

Peng-Fei Lian, Zi-Hao Li, Xin-Yue Qiu, Tong-Mei Ding, Shu-Yu Zhang

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引用次数: 0

摘要

实现了烯炔酮与磺酸钠之间高效的级联 1,6 加成/环化/对映体选择性质子化途径。在温和的反应条件下，该方法能以良好的产率和较高的对映选择性获得各种磺酰基取代的呋喃。通过对照实验和密度泛函理论计算，阐明了合理的反应机理和立体选择性的来源。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Organocatalytic Asymmetric Synthesis of Sulfonyl-Substituted Furans via a Cascade 1,6-Addition/Cyclization/Enantioselective Protonation Pathway

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Organocatalytic Asymmetric Synthesis of Sulfonyl-Substituted Furans via a Cascade 1,6-Addition/Cyclization/Enantioselective Protonation Pathway

An efficient cascade 1,6-addition/cyclization/enantioselective protonation pathway between ene–yne–ketones and sodium sulfinates was realized. This protocol provides practical access to various sulfonyl-substituted furans in good yields and high enantioselectivities under mild reaction conditions. Control experiments and density functional theory calculations were conducted to elucidate the plausible reaction mechanism and the origins of stereoselectivity.

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来源期刊

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.