高等学校化学学报 ›› 2000, Vol. 21 ›› Issue (S1): 432.
• Synthetic Sciences • 上一篇 下一篇
WU Xin-Yan1, TANG Fan-Yi1, XU Hua-Dong1, ZHOU Qi-Lin2
WU Xin-Yan1, TANG Fan-Yi1, XU Hua-Dong1, ZHOU Qi-Lin2
摘要:
Palladium-catalyzed arylation and alkenylation of olefins, known as the Heck reaction, is one of the most efficient catalytic methods for carbon-carbon bond formation in organic synthesis[1]. During the last decade, asymmetric Heck reactions have attracted great attention, and a number of highly enantioselective chiral ligands have been developed to enhance chiral discrimination in these reactions[2]. However, asymmetric Heck-type hydroarylations of olefins, addition of aryl halides or triflates to carbon-carbon double bonds, have not been well studied. In 1991, Brunner reported an asymmetric hydroarylation of norbornene and norbornadiene with aryl iodides using chiral bisphosphine ligands, and around 40% ee was achieved[3]. Later on, Achiwa reached around 70% ee in the asymmetric hydroarylation of norbornene with phenyl triflate by using chiral P-N ligands[4,5]. Herein, we wish to describe our investigations on chiral quinolinyl-oxazoline ligands that provide the first examples of efficient bisnitrogen ligands in Heck-type hydroarylation and the application of this reaction in the asymmetric synthesis of Epibatidine.
TrendMD: