A highly stereoselective preparation of optically active alkenyl substituted allene compounds and methods for their construction

By using palladium catalyst and chiral phosphoramide ligand to catalyze the asymmetric cross-coupling reaction of propargyl alcohol derivatives with alkenyl borate esters, the problems of harsh reaction conditions and limited functional group compatibility in the synthesis of alkenyl substituted allenes in the prior art are solved, and the synthesis of optically active alkenyl substituted allenes is realized in a high-efficiency and simple manner.

CN122404093APending Publication Date: 2026-07-17SHANGHAI UNIV
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Patent Information

Authority / Receiving Office
CN · China
Patent Type
Applications(China)
Current Assignee / Owner
SHANGHAI UNIV
Filing Date
2026-04-30
Publication Date
2026-07-17

AI Technical Summary

Technical Problem

Existing technologies for synthesizing alkenyl-substituted allene compounds suffer from harsh reaction conditions, limited functional group compatibility, difficulty in obtaining chiral products, and low efficiency.

Method used

Optically active alkenyl-substituted allene compounds were constructed by using a complex formed by a palladium catalyst and a chiral phosphoramidite ligand to catalyze the asymmetric cross-coupling reaction of propargyl alcohol derivatives and alkenyl borate esters.

Benefits of technology

It achieves highly stereoselective and regioselective synthesis of alkenyl-substituted allenes, with a wide range of applicable substrates, strong functional group tolerance, mild reaction conditions, simple operation, low cost, and is suitable for laboratory and industrial-scale preparation.

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Abstract

本发明公开了一种高立体选择性制备光学活性烯基取代联烯化合物及其构建方法,该方法的核心在于构建了一个高效的催化体系,即选用炔丙醇衍生物作为亲电试剂前体,烯基硼酸酯类化合物作为亲核试剂,采用过渡金属钯与手性亚磷酰胺配体的配合物为催化剂。在上述条件下,反应能够以极高的立体选择性进行,直接构建出结构复杂的光学活性烯基取代联烯化合物。与现有技术相比,本发明具有操作简便与经济性、优异的立体控制能力、广泛的底物普适性等优点。
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