Control of Regioselectivity in Pd(0)-Catalyzed Coupling−Cyclization Reaction of 2-(2‘,3‘-Allenyl)malonates with Organic Halides
作者:Shengming Ma、Ning Jiao、Shimin Zhao、Hairong Hou
DOI:10.1021/jo0108616
日期:2002.5.1
in the Pd(0)-catalyzed coupling-cyclization of 2-(2',3'-allenyl)malonates with organic halides is determined by the steric and electronic effects of both substrates. By deliberate control of the reaction conditions, the regioselectivity of this reaction can be tuned. With conditions A and B, the reaction afforded vinylic cyclopropane derivatives, while with conditions C and D, the reaction afforded
在Pd(0)催化的2-(2',3'-烯基)丙二酸酯与有机卤化物的偶合偶联环化中的区域选择性取决于两个底物的空间和电子效应。通过控制反应条件,可以调节该反应的区域选择性。在条件A和B下,反应得到乙烯基环丙烷衍生物,而在条件C和D下,反应以高度选择性的方式得到环戊烯衍生物。在类似条件下,1-烯基卤化物倾向于形成更多的三元环状产物。在丙二烯部分和芳基卤化物的2'-位上增加的空间位阻有利于五元环状产物的形成。