O-Phosphination of Aldehydes/Ketones toward Phosphoric Esters: Experimental and Mechanistic Studies

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2020-06-02 DOI:10.1021/acs.orglett.0c01537

Yanyan Qian, Qiang Dai, Zhiming Li*, Yu Liu*, Junliang Zhang*

引用次数: 18

Abstract

Addition of P–H species to carbonyl groups, namely the Pudovik reaction, normally delivers hydroxyl phosphorus compounds, along with phosphate byproducts in some cases. A few controllable systems starting from phosphites were set up to mainly provide the phosphates. Herein, we present a highly selective protocol starting from phosphonate precursors leading to phosphinate derivatives. Enantioenriched phosphinates were successfully achieved from chiral phosphine oxide precursors. Experimental and theoretical investigations were conducted to understand the mechanistic details.

Abstract Image

查看原文本刊更多论文

醛/酮向磷酸酯的o -磷酸化:实验和机理研究

将P-H基团加到羰基上，即Pudovik反应，通常会产生羟基磷化合物，在某些情况下还会产生磷酸盐副产物。建立了几个以亚磷酸盐为起始原料的可控体系，主要提供磷酸盐。在这里，我们提出了一个高度选择性的方案，从磷酸盐前体到磷酸盐衍生物。从手性氧化膦前体成功制备了富对映体膦酸盐。进行了实验和理论研究，以了解机理细节。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

求助全文

约1分钟内获得全文求助全文

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.