1-Arylallyloxysilanes as Formal Precursors to Ketone-Derived Potassium Homoenolate Equivalents

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-04-28 DOI:10.1021/acs.orglett.5c01177

Shuto Okuda, Yutaka Narita, Rikuo Hayashi, Taro Udagawa, Masahiro Sai

引用次数: 0

Abstract

This paper reports the successful conversion of 1-arylallyloxysilanes into highly nucleophilic siloxyallylpotassium intermediates using (trimethylsilyl)methylpotassium as the base. These organopotassium species react regioselectively with various electrophiles, leading to the formation of the corresponding 3-functionalized (Z)-silyl enol ethers. The resulting silyl enol ethers can undergo a range of α-functionalization reactions, yielding ketones with diverse structures. Thus, our method enables the effective utilization of 1-arylallyloxysilanes as formal precursors to ketone-derived potassium homoenolate equivalents.

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1-芳烯丙烯氧基硅烷作为酮衍生的同烯酸钾等价物的形式前体

本文报道了以（三甲基硅基）甲基钾为碱，成功地将1-芳基烯丙氧基硅烷转化为高度亲核的硅氧烯基钾中间体。这些有机钾与各种亲电试剂发生区域选择性反应，形成相应的3功能化(Z)-硅基烯醇醚。得到的硅烯醇醚可以发生一系列α-官能化反应，生成不同结构的酮类。因此，我们的方法能够有效地利用1-芳烯丙烯氧基硅烷作为酮衍生的纯烯酸钾当量的正式前体。

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.