Cobalt Porphyrin Catalyzed [3+2] Cycloaddition of Cyclopropanes and Carbonyl Compounds

Abstract

A cobalt porphyrin efficiently catalyzed the formal [3+2] cycloaddition of alkyl-/aryl-substituted cyclopropanes and carbonyl compounds such as aldehydes and ketones to afford the corresponding substituted tetrahydrofurans. The use of the cobalt porphyrin complex as a Lewis acid to catalyze the reaction via the electrophilic activation of cyclopropanes was demonstrated. The high functional-group tolerance and robustness of the catalyst were also demonstrated. Further, the potential utility of the catalyst was demonstrated by performing the cycloaddition of cyclic ketones and cyclopropanes to afford spiro tetrahydrofurans.

Progress in Transition-Metal-Catalyzed Carbonylative Cycloadditions Using Carbon Monoxide

“…2000 年, Murai 课题组 [130] 报道了钌催化的环丙基亚 胺 7.8 与 CO 的环加成反应(Scheme 29). 当底物 7.8 中氮 原子上的取代基为叔丁基和环己基时, 反应才能以较高 的产率生成六元不饱和内酰胺 7.9. de Meijere 课题组 [128]…”