Phosphonamidates of Camphorsultam: Versatile Building Blocks for the Synthesis of P‐Chiral Phosphorous(V) Compounds

IF 4.4 2区化学 Q2 CHEMISTRY, APPLIED

Advanced Synthesis & Catalysis Pub Date : 2024-11-27 DOI:10.1002/adsc.202401268

Yasutomo Yamamoto, Yurika Kambara, Ayase Matsumoto, Miku Murata, Mizuki Nakamoto, Tomoe Ishiura, Sakura Nakai, Hideyasu China, Kenji Watanabe, Akari Miyawaki, Junpei Matsuoka

引用次数: 0

Abstract

Camphorsultam was utilized for the optical resolution of P‐chiral phosphorous compounds. After chromatographic separation of diastereomeric RP‐ and SP‐ phosphonamidate intermediates, subsequent substitution reactions with phenol derivatives yielded P‐chiral phosphonic acid aryl esters with excellent enantioselectivities. In these processes, chiral sulfonamide of camphorsultam demonstrated superior abilities as an optical‐resolving agent and a good leaving group. This method was applied to the synthesis of P‐chiral phosphinic esters, phosphonamidates, and thiophosphonate diesters.

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樟脑磺酰胺：合成 P 手性磷（V）化合物的多功能基石

利用樟脑磺胺对P手性磷化合物进行光学解析。在色谱分离非对映RP-和SP；- 在膦酰胺中间体中，随后与苯酚衍生物发生取代反应，可得到手性膦酸芳基酯，并具有极佳的对映选择性。在这些过程中，樟脑磺酰胺手性磺酰胺作为光学分解剂和良好的离去基团表现出了卓越的能力。该方法被应用于合成手性膦酸酯、膦酸酰胺和硫代膦酸二酯。

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.