Enantioselective Synthesis of P-Chiral Phosphine Oxides Bearing an All-Carbon Quaternary Stereogenic Center via Palladium-Catalyzed Domino Heck–Suzuki Reaction

IF 11.3 1区化学 Q1 CHEMISTRY, PHYSICAL

ACS Catalysis Pub Date : 2024-09-20 DOI:10.1021/acscatal.4c04958

Siyu Zhao, Jiahao Liu, Xunfang Xu, Xuemei Chen, Terumasa Kato, Zhe Wang, Yan Liu, Keiji Maruoka

引用次数: 0

Abstract

An approach has been developed for the enantioselective synthesis of P-chiral phosphine oxides bearing an all-carbon quaternary stereogenic center via a Pd-catalyzed domino Heck–Suzuki reaction. The origin of the mechanistic preference leading to high diastereo- and enantioselectivities under the Pd catalysis based on a TADDOL-derived phosphoramidite ligand was rationalized on the basis of DFT calculations.

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通过钯催化多米诺 Heck-Suzuki 反应，对映选择性合成带有全碳季态中心的 P 手性氧化膦

通过钯催化的多米诺 Heck-Suzuki 反应，开发了一种对映选择性合成带有全碳季立体中心的 P 手性膦氧化物的方法。在 DFT 计算的基础上，对基于 TADDOL 衍生的膦酰胺配体的钯催化下导致高非对映和对映选择性的机理偏好的起源进行了合理化。

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

ACS Catalysis CHEMISTRY, PHYSICAL-

CiteScore

20.80

自引率

6.20%

发文量

1253

审稿时长

1.5 months

期刊介绍： ACS Catalysis is an esteemed journal that publishes original research in the fields of heterogeneous catalysis, molecular catalysis, and biocatalysis. It offers broad coverage across diverse areas such as life sciences, organometallics and synthesis, photochemistry and electrochemistry, drug discovery and synthesis, materials science, environmental protection, polymer discovery and synthesis, and energy and fuels. The scope of the journal is to showcase innovative work in various aspects of catalysis. This includes new reactions and novel synthetic approaches utilizing known catalysts, the discovery or modification of new catalysts, elucidation of catalytic mechanisms through cutting-edge investigations, practical enhancements of existing processes, as well as conceptual advances in the field. Contributions to ACS Catalysis can encompass both experimental and theoretical research focused on catalytic molecules, macromolecules, and materials that exhibit catalytic turnover.