Catalytic Phosphine-Enabled Direct δ-Addition of Substituted Allenoates to Nitroalkenes: A Route to 1,3-Dienes and 1,3,5-Trienes

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-20 DOI:10.1021/acs.orglett.6c03903

Jinlong Li,Shulei Pan,Ning Wang,Kaiyun Liu,Jing Ren,Xinyu Long,Kaizhi Li

引用次数: 0

Abstract

Conjugated polyene represents a ubiquitous structural motif found in natural products and pharmaceutical agents. In this study, we demonstrate that γ-substituted allenoates can act as nucleophilic C4 synthon equivalents of dienes under phosphine catalysis, enabling their efficient addition with nitroalkenes to afford β-nitro 1,3-diene derivatives in moderate to good yields. This transformation features a remarkably broad substrate scope and good functional group compatibility, and it can be applied to the late-stage functionalization of complex natural product derivatives. The utility of the resulting β-nitro conjugated dienes is further demonstrated through subsequent transformations, affording a diverse library of conjugated triene compounds. A plausible reaction mechanism along with representative applications are also discussed.

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催化磷化氢催化取代烯丙酸酯直接δ加成到硝基烯烃：一条生成1,3-二烯和1,3,5-三烯的途径

共轭多烯是天然产物和药物制剂中普遍存在的结构基序。在本研究中，我们证明了在膦催化下，γ-取代的烯酸盐可以作为亲核的二烯的C4合成物，使它们能够与硝基烯有效加成，以中等到较高的产量获得β-硝基1,3-二烯衍生物。这种转化具有非常广泛的底物范围和良好的官能团相容性，可应用于复杂天然产物衍生物的后期功能化。由此产生的β-硝基共轭二烯的效用通过随后的转化进一步证明，提供了不同的共轭三烯化合物库。还讨论了一种可行的反应机理及其典型应用。

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

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.