The State Key Laboratory of Elemento-Organic Chemistry and Department of Chemistry, Nankai University, 94 Weijin Road, Tianjin 300071, P. R. China.
Org Lett. 2012 Feb 17;14(4):996-9. doi: 10.1021/ol2032569. Epub 2012 Feb 3.
An amine-catalyzed [4 + 2] annulation of Morita-Baylis-Hillman allylic acetates 2 with electron-deficient alkenes or diazenes has been developed for efficient syntheses of highly functionalized cyclohexenes, tetrahydropyridazines, and important spirocycles. This reaction unveils a new reactivity pattern of the intensely studied allylic compounds 2 acting as a C(4) synthon in Lewis base catalyzed annulation reactions and also showcases divergent catalysis between tertiary amines and phosphines.
已开发出一种胺催化的[4+2]环化反应,用于 Morita-Baylis-Hillman 烯丙基乙酸盐 2 与缺电子烯烃或重氮化合物的高效合成,得到高度官能化的环己烯、四氢吡啶嗪和重要的螺环化合物。该反应揭示了强烈研究的烯丙基化合物 2 的一种新反应模式,作为路易斯碱催化环化反应中的 C(4)合成子,同时还展示了叔胺和膦之间的分歧催化作用。