Sulfinamide Synthesis Using Organometallic Reagents, DABSO, and Amines

被引：36

作者：

Lo, Pui Kin Tony ^{[1
]}

Oliver, Gwyndaf A. ^{[1
]}

Willis, Michael C. ^{[1
]}

机构：

[1] Univ Oxford, Dept Chem, Chem Res Lab, Mansfield Rd, Oxford OX1 3TA, England

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 09期

基金：

英国工程与自然科学研究理事会;

关键词：

ASYMMETRIC-SYNTHESIS; GENERAL-METHOD; SULFONIMIDAMIDES; SULFOXIMINES; DERIVATIVES; ALDIMINES; SULFONES; ALCOHOLS; UTILITY; ACIDS;

D O I：

10.1021/acs.joc.0c00334

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We report the synthesis of sulfinamides using organometallic reagents, a sulfur dioxide reagent, and nitrogen based-nucleophiles. The addition of an organometallic reagent to the commercially available sulfur dioxide surrogate, DABSO, generates a metal sulfinate which is reacted with thionyl chloride to form a sulfinyl chloride intermediate. Trapping the sulfinyl chlorides in situ with a variety of nitrogen nucleophiles delivers sulfinamides in 32-83% yields. Each stage of the process is performed at room temperature, and the total reaction time is only 1.5 h.

引用

页码：5753 / 5760

页数：8

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