Palladium(0)-Catalyzed Asymmetric Cross Inverse-Electron-Demand Diels-Alder Reaction between Distinct Electron-Deficient Dienes.

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-18 DOI:10.1021/acs.orglett.5c01957

Ke Xie,Bao-Rui Kong,Chuang-Qi Wang,Zhi-Chao Chen,Wei Du,Ying-Chun Chen

引用次数: 0

Abstract

Here we present an asymmetric and regioselective cross inverse-electron-demand Diels-Alder reaction between 2,4-dienyl carbonyls and 1-heterodienes or allylidenemalononitriles, by reversing the reactivity of the former electrophilic partners via γ,δ-dihapto coordination with palladium(0) and backdonation. A broad spectrum of multifunctional tetrahydropyridines, dihydropyrans and cyclohexene derivatives are generally constructed in high yields, diastereo- and enantioselectivity, even with low catalyst loadings (0.6 mol % of Pd).

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钯(0)催化不同缺电子二烯之间的不对称交叉逆电按需二烯- alder反应。

本研究提出了2,4-二烯基羰基与1-杂二烯或烯丙基二烯腈之间的不对称和区域选择性交叉反电按需diols - alder反应，通过与钯(0)的γ、δ-二hapto配位和反给体逆转了前亲电伙伴的反应活性。广泛的多功能四氢吡啶、二氢吡喃和环己烯衍生物通常具有高产率、非映对和对映选择性，甚至在低催化剂负载（0.6 mol %的Pd）下也能构建。

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.