One‐pot Unsymmetrical Ketone Synthesis Employing a Pyrrole‐Bearing Formal Carbonyl Dication Linchpin Reagent
作者:Stephen T. Heller、James N. Newton、Tingting Fu、Richmond Sarpong
DOI:10.1002/anie.201502894
日期:2015.8.17
synthesis of unsymmetrical ketones utilizing a pyrrole‐bearing carbonyl linchpin reagent (carbonyl linchpin N,O‐dimethylhydroxylamine pyrrole; CLAmP) is reported. In contrast to other carbonyl dielectrophile equivalents, CLAmP enables the synthesis of ketones from a variety of organolithium and Grignard reagents. The electrophilic nature of CLAmP enables the addition of less reactive as well as thermally
报道了使用带有吡咯的羰基兰克平试剂(羰基兰克平N,O-二甲基羟胺吡咯; CLAmP)进行一锅法合成不对称酮的方法。与其他羰基双亲电子试剂等效物相比,CLAmP能够从多种有机锂和格氏试剂中合成酮。CLAmP的亲电子性质使得可以添加反应性和热不稳定亲核试剂。CLAmP被设计为在添加有机金属亲核试剂后形成动力学稳定的四面体中间体。通过原位红外研究获得了持久性四面体中间体的存在的证据。