Department of Applied Chemistry, National Chiao Tung University, 1001 University Road, Hsinchu 30010, Taiwan.
Chem Commun (Camb). 2019 Jan 25;55(8):1116-1119. doi: 10.1039/c8cc09817d. Epub 2019 Jan 9.
The direct N1-selective allylation of indoles with allylic alcohols has been accomplished by synergistic functions of palladium catalysts and titanium tetraisopropoxide. The site selectivity is notably different from that observed in other related transition metal-catalyzed approaches. This chemistry provides a facile route to a variety of allylated indoles in synthetically useful yields. The utility of this simple allylation reaction was demonstrated with the first total synthesis of (+)-N-(4'-hydroxyprenyl)-cyclo(alanyltryptophyl), which was completed in five steps, starting from l-tryptophan methyl ester hydrochloride.
钯催化剂和钛四异丙醇盐的协同作用实现了吲哚与烯丙醇的直接 N1 选择性烯丙基化反应。该反应的位点选择性与其他相关过渡金属催化方法观察到的明显不同。这种化学方法为各种烯丙基吲哚的合成提供了一种简便的途径，产率高。该简单的烯丙基化反应的实用性通过 (+)-N-(4'-羟基赖氨酰)-环(丙氨酰色氨酰)的首次全合成得到了证明，该合成从 l-色氨酸甲酯盐酸盐开始，经过五步反应完成。
