Palladium-Catalyzed Asymmetric Allylic Substitutions Achieved by C–N Axially Chiral N-Arylpyrrole Derived Monophosphine Ligands

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED Advanced Synthesis & Catalysis Pub Date : 2024-07-30 DOI:10.1002/adsc.202400206

Shiping Zhong, Jianwei Zhou, Boda Li, Zunting Zhang, Tao Wang

引用次数: 0

Abstract

Monophosphine ligands based on C–N axially chiral N-Arylpyrrole backbones are prepared starting from amino acids and evaluated in Pd-catalyzed asymmetric allylic substitutions. 20.7- 99.9% ees are achieved in the reactions of rac-1,3-diphenylallyl acetates with O-, N- and C-nucleophiles. Ligand screening revealed that the steric hindrance from 3- or 4- position of the pyrrole is crucial for the enantioselectivity of the reaction. The synthetic utilization of the products was demonstrated by the transformation of one product by a gold-catalyzed oxidative rearrangement reaction.

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钯催化 C-N 轴向手性 N-芳基吡咯衍生单膦配体实现的不对称烯丙基取代

以氨基酸为起点，制备了基于 C-N 轴手性 N-Arylpyrrole 骨架的单膦配体，并在 Pd 催化的不对称烯丙基取代反应中进行了评估。在 rac-1,3-diphenylallyl acetates 与 O-、N- 和 C-亲核物的反应中，实现了 20.7%- 99.9% 的 ees。配体筛选显示，吡咯的 3-或 4-位置的立体阻碍对反应的对映选择性至关重要。通过金催化氧化重排反应转化一种产物，证明了这些产物的合成用途。

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

Advanced Synthesis & Catalysis 化学-应用化学

CiteScore

9.40

自引率

7.40%

发文量

447

审稿时长

1.8 months

期刊介绍： Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry. The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.