Chiral Bis-8-Aryl-isoquinoline Bis-alkylamine Iron Catalysts for Asymmetric Oxidation Reactions

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-01-22 DOI:10.1021/acs.orglett.5c0005010.1021/acs.orglett.5c00050

Tomer Mintz, Lei Liu and Doron Pappo*,

引用次数: 0

Abstract

A novel class of bis-8-aryl-isoquinoline (^AriQ) bis-alkylamine iron complexes, Fe^II(^AriQ₂dp)(OTf)₂ and Fe^II(^AriQ₂mc)(OTf)₂ (dp = dipyrrolidinyl or mc = N,N′-dimethylcyclohexyl-diamine), for asymmetric oxidation reactions is reported. The scalable divergent synthesis of 8-aryl-3-formylisoquinolines (8), the key intermediates in preparing these ligands, enables precise structural and electronic tuning around the metal center. The enantioselective epoxidation and hydroxy carbonylation of conjugated alkenes, mediated by the Fe^II(^3,5-di-CF₃iQ₂dp) catalyst with H₂O₂ as the oxidant, demonstrates the potential of these redox Fe^II[N₄] catalysts in inducing face selection in oxygen transfer transformations.

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不对称氧化反应的手性双-8-芳基异喹啉双-烷基胺铁催化剂

报道了一类用于不对称氧化反应的新型双-8-芳基异喹啉（AriQ）双烷基胺铁配合物FeII(AriQ2dp)(OTf)2和FeII(AriQ2mc)(OTf)2 （dp =二吡咯烷基或mc = N,N ' -二甲基环己基二胺）。8-芳基-3-甲酰基异喹啉(8)是制备这些配体的关键中间体，可扩展的发散合成可以在金属中心周围进行精确的结构和电子调谐。以H2O2为氧化剂的FeII（3,5-di- cf3iq2dp）催化剂介导共轭烯烃的对映选择性环氧化和羟基羰基化反应，证明了这些氧化还原FeII[N4]催化剂在氧转移转化中诱导面选择的潜力。

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.