Iridium-Catalyzed Asymmetric Allylation of Silyl Enol Ethers Derived from α-Ketoesters and α-Diketones with Allylic Alcohols

IF 4.9 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-02-28 DOI:10.1021/acs.orglett.5c00244
Takahiro Sawano, Natsuki Suzuki, Kana Takahashi, Yuta Goto, Kazunori Miyashita, Ryo Takeuchi
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Abstract

We report an asymmetric allylation of silyl enol ethers derived from α-ketoesters with allylic alcohols by an iridium/chiral (P,olefin)-ligand catalyst. Allylation with a broad range of silyl enol ethers and allylic alcohols formed the allylated products with excellent enantioselectivities. Silyl enol ethers derived from α-diketones as well as α-ketoesters were also compatible with the asymmetric allylation to achieve nearly perfect enantioselectivities. The utility of allylated products bearing an α-ketoester group and an α-diketone group is demonstrated by transformation to valuable functional groups, exemplified by α-aminoester, aldehyde, 2(1H)-quinoxalinone, and quinoxaline.

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我们报告了在铱/手性(P,烯烃)配位催化剂的作用下,α-酮酯衍生的硅基烯醚与烯丙基醇的不对称烯丙基化反应。与多种硅基烯醇醚和烯丙基醇进行烯丙基化反应生成的烯丙基化产物具有极佳的对映选择性。由 α-二酮类化合物和 α-酮类化合物衍生的硅烯醇醚也能与不对称烯丙基化反应相容,从而获得近乎完美的对映选择性。α-氨基酯、醛、2(1H)-喹喔啉酮和喹喔啉等有价值的官能团的转化证明了带有α-酮基和α-二酮基的烯丙基化产物的用途。
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来源期刊
Organic Letters
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.
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