基于3-烯基吲哚的不对称烷基化反应研究

申请人青年基金项目“基于3-吲哚甲基胺的不对称烷基化反应研究”取得了连续性的研究成果。申请人课题组在手性酸催化的不对称间接烷基化反应、直接烷基化反应，以及通过相关烷基化反应合成手性cyclopenta[b]indole化合物上进行了逐步深入的研究。在Angew. Chem., Org. Lett. 等化学杂志上发表研究论文5篇，单篇引用达40次。相关工作被Synfacts，《有机化学》和《化学通报》作了亮点介绍。.本项目将研究在手性有机分子催化下，3-烯基吲哚分别与醛酮和二芳基甲基醇的不对称alfa-烷基化反应和不对称付-克烷基化反应；还将通过该项目的相关方法学合成结构复杂的手性吲哚化合物。这是首次将取代烯烃作为醛酮的烷基化试剂，也是首次将富电子烯烃作为不对称付-克烷基化反应的给体。本项目将给不对称烷基化反应给体和受体的拓展以及手性吲哚化合物的设计合成带来新的思路。

The continuous research achievements were obtained in our project “The Asymmetric Alkylation of 3-indolylamines”. We developed efficient methodologies for the asymmetric indirect alkylation reaction, direct alkylation reaction, as well as the sythesis of chiral cyclopenta[b]indoles. 5 Research papers were published on Angew. Chem., Org. Lett., J. Org. Chem. et. al. One of them was cited 40 times. Our research work published in Org. Lett. (2009, 11, 4620) was highlighted by Synfacts and our work published in Angew. Chem. Int. Ed. (2012, 51, 1899) was highlighted by Chinese Science Bulletin and Chinese Journal of Organic Chemistry, respectively..As a continuation of our research in asymmetric alkylation reaction, we will investigate the asymmetric alfa-alkylation of carbonyl compounds and the Friedel-Crafts reaction with biarylmethanols by using 3-vinylindoles as acceptors and donors, respectively. This is the first time to use alkenes as alkylation reagents of aldehydes and ketones by organocatalysis, also the first time to introduce electron-rich alkenes into the asymmetric Friedel-Crafts alkylation reactions. We will also apply our methodologies to the synthesis of structural diversity chiral indoles. We believe that our project has scientific value in expanding the acceptors and donors in alkylation reaction, as well as the chiral indole synthesis.