Iridium-Catalyzed, Highly Selective Allylation of Pyrazolones for the Convenient Construction of Adjacent Stereocenters

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-11-22 DOI:10.1021/acs.orglett.4c03586

Shixiang Sun, Yuqi Zhang, Martin G. Banwell, Lorenzo V. White, Leijie Zhou

引用次数: 0

Abstract

This paper describes an iridium-catalyzed allylation of ring-fused pyrazolones that proceeds with excellent regio-, diastereo- and enantio-selectivities. The approach exploits unactivated, racemic allylic alcohols as a source of allyl building blocks. Asymmetric syntheses of a series of biologically relevant, chiral pyrazolones highlight the utility of the methodology. The use of Cu(OTf)₂ as a co-catalyst greatly enhances the regioselectivity of the reaction and permits selective syntheses of branched allylation products.

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铱催化吡唑酮的高选择性烯丙基化，方便构建相邻立体中心

本文介绍了一种铱催化的环融吡唑酮烯丙基化反应，该反应具有极佳的区域、非对映和对映选择性。该方法利用未活化的外消旋烯丙基醇作为烯丙基结构单元的来源。一系列与生物相关的手性吡唑酮的不对称合成凸显了该方法的实用性。使用 Cu(OTf)2 作为辅助催化剂大大提高了反应的区域选择性，并允许选择性合成支链烯丙基化产物。

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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.