A Chiral Phosphoric Acid Structure Leads to Strong Interactions That Affected Selectivity of the N-Hydroxyalkylation Reactions: A Density Functional Theory Study

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2026-10-15 DOI:10.1021/acs.orglett.6c03162

Ran Zhang,ZiHao Li,ShuYu Zhang,Abing Duan

引用次数: 0

Abstract

Abstract Chiral phosphoric acids (CPAs) can regulate reaction selectivity via catalyst–substrate noncovalent interactions (NCIs). Most studies remain macroscopic and have not addressed how CPA structures modulate the interaction strength and thereby selectivity. This study reveals that, in CPA-catalyzed N-hydroxyalkylation reactions, the CPA backbone rigidity and substituent structure promote stronger interactions, thereby enhancing enantioselectivity. An ordered π system facilitates the formation of more pronounced π–π stacking.

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手性磷酸结构导致影响n -羟基烷基化反应选择性的强相互作用：密度泛函理论研究

手性磷酸（CPAs）通过催化-底物非共价相互作用（NCIs）调控反应选择性。大多数研究仍然是宏观的，没有解决CPA结构如何调节相互作用强度从而调节选择性。本研究表明，在CPA催化的n -羟基烷基化反应中，CPA的主链刚性和取代基结构促进了更强的相互作用，从而提高了对映体选择性。有序π体系有利于形成更明显的π -π堆积。

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.