Iridium-catalyzed asymmetric cascade allylation/lactonization of methyl salicylates: enantioselective construction of chiral benzodioxepinones

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2024-11-05 DOI:10.1039/d4qo01771d

Bendu Pan, Yunru Wu, Yaqi Zhang, Xiaobo He, Long Jiang, Liqin Qiu

引用次数: 0

Abstract

An efficient asymmetric cascade allylation/lactonization of methyl salicylates has been achieved. The utilization of chiral-bridged biphenyl phosphoramidite ligand L3 resulted in good yields (up to 85%) and enantioselectivity (up to 95% ee) for the construction of a wide range of chiral benzodioxepinones with tolerance to diverse substituents. This reaction is featured by low catalyst loading, commercially available substrates and a broad substrate scope. Control experiments indicate that a relay catalytic pathway and kinetic resolution of racemic VEC might occur. In this transformation, the chiral-bridged phosphoramidite ligand L3 shows some advantages in enantioselective control compared to its BINOL-derived counterpart.

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铱催化水杨酸甲酯的不对称级联烯丙基化/内切：手性苯并二氧杂环庚酮的对映选择性构建

实现了水杨酸甲酯的高效不对称级联烯丙基化/内酯化。利用手性桥接联苯磷酰胺配体 L3，可以获得良好的产率（高达 85%）和对映选择性（高达 95% ee），从而构建出多种手性苯并二氧杂环庚酮，并能耐受不同的取代基。该反应的特点是催化剂负载量低、底物可从市场上买到且底物范围广。对照实验表明，可能会出现外消旋 VEC 的中继催化途径和动力学解析。在这一转化过程中，手性桥接磷酰胺配体 L3 与 BINOL 衍生的配体相比，在对映体选择性控制方面具有一定优势。

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 Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.