Switchable reactivity of acylated α,β-dehydroamino ester in the Friedel-Crafts alkylation of indoles by changing the Lewis acid
Switchable reactivity of acylated α,β-dehydroamino ester in the Friedel-Crafts alkylation of indoles by changing the Lewis acid
复制标题
DOI：
10.1021/jo800881u
复制
发表时间：
2008-07-18
影响因子：
3.6
通讯作者：
Piersanti, Giovanni
中科院分区：
文献类型：
--
作者：
Angelini, Elena;Balsamini, Cesarino;Piersanti, Giovanni
在不同过渡金属盐的促进下，实现了吲哚与N-乙酰化α，β-脱氢丙氨酸甲酯的高度区域选择性亲电取代。正交区域选择性提供了一个有效的协议，高度官能化的3-吲哚基-α-氨基酸。通过核磁共振研究探讨了反应机理。
Highly regioselective electrophilic substitution of indoles with N-acetylated alpha,beta-dehydroalanine methyl ester, promoted by different transition metal salts was achieved. The orthogonal regioselectivity provides an efficient protocol toward highly functionalized 3-indolyl-alpha-amino acids. The mechanism of the reactions was explored by NMR studies.