Catalytic Asymmetric Intramolecular Domino Allylic O-Alkylation/Allylic Dearomatization of Allyl Aryl Ethers

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-06-02 DOI:10.1021/acs.orglett.5c01540

Yun-Qiao Zhang, Ying-Long Li, Ke-Xu Wang, Dong-Chao Wang, Hai-Ming Guo

引用次数: 0

Abstract

An intramolecular asymmetric allylic O-alkylation/allylic dearomative spirocyclization cascade has been successfully developed with allyl aryl ethers. In the presence of palladium and a phosphoramidite ligand, a series of spirocyclohexadienones with an exocyclic double bond were obtained in up to 98% yield with 98% ee. The asymmetric allylic alkylation mechanism was elucidated through control experiments. In addition, scale-up of the reaction and further transformations of the spirocyclic products were also performed, demonstrating the potential application of this method.

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催化分子内不对称多米诺烯丙基o -烷基化/烯丙基芳基醚脱芳化

以烯丙基芳基醚为原料，成功地建立了分子内不对称烯丙基o -烷基化/烯丙基去芳香螺旋环化级联反应。在钯和磷酰胺配体的存在下，以98%的ee和98%的收率得到了一系列具有外环双键的螺环己二烯酮。通过对照实验阐明了烯丙基不对称烷基化机理。此外，还进行了反应的放大和螺旋环产物的进一步转化，证明了该方法的潜在应用。

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.