Enantioselective Copper-Catalyzed Desymmetric Olefination via the Boron-Wittig Reaction

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2025-07-07 DOI:10.1021/acscatal.5c02755

Dongzhen Xu, Weike Li, Wenze Shi, Xihong Wang, Min Wang, Jian Liao

引用次数: 0

Abstract

Boron-Wittig reactions represent one of the important tools for stereoselective synthesis of multisubstituted alkenes. However, using this strategy to build chiral frameworks is an extreme challenge. Here, we present an enantioselective boron-Wittig olefination of bis[(pinacol)boron]methane with biaryl dialdehydes. This protocol was facilitated by a Cu/SOP catalytic system and offered an efficient desymmetrization for the synthesis of axially chiral aryl alkenes. The good reactivity, outstanding selectivity (chem and enantio), broad substrate and functionality tolerance, and diverse product transformations ensured the potential broad applicability. The stereoselectivity of the reaction was intricately linked to a halogen ion, and a reasonable catalytic cycle was proposed.

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铜催化硼-维蒂格反应的对映选择性不对称烯烃反应

硼-维蒂格反应是立体选择性合成多取代烯烃的重要手段之一。然而，使用这种策略来构建手性框架是一个极端的挑战。在这里，我们提出了一种双芳基二醛对映选择性双[（蒎酚）硼]甲烷的硼-维提格烯烃。该工艺在Cu/SOP催化体系下进行，为轴手性芳基烯烃的合成提供了高效的脱对称反应。良好的反应性，突出的选择性（化学和对映），广泛的底物和功能耐受性，以及多样化的产物转化确保了潜在的广泛适用性。该反应的立体选择性与卤素离子有复杂的联系，并提出了合理的催化循环。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.