Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL, 60607 (USA).
Angew Chem Int Ed Engl. 2014 Mar 17;53(12):3197-200. doi: 10.1002/anie.201309435. Epub 2014 Feb 12.
Installation of amino functionality on organic molecules through direct CN bond formation is an important research objective. To achieve this goal, a 1,2-aminocyanation reaction was developed. The reaction occurs through the formation of pyrazolines by means of a formal dipolar cycloaddition of cyclic α,β-unsaturated ketones with lithium trimethylsilyldiazomethane followed by novel protonolytic N-N bond cleavage under mild conditions. This two-step process provides a diverse array of structurally complex free and mono-alkylated α-amino ketones in excellent yields.
在有机分子上通过直接 CN 键形成来引入氨基官能团是一个重要的研究目标。为了实现这一目标，开发了 1,2-氨基氰化反应。该反应通过环状α,β-不饱和酮与三甲基硅基锂重氮甲烷的形式双极性环加成形成吡唑啉，然后在温和条件下通过新型质子化 N-N 键断裂来进行。这个两步过程以优异的收率提供了多种多样结构复杂的游离和单烷基化的α-氨基酮。
