1-Hydroxy-2-methyl-2-propyl Isocyanide (HMPI) as a New Convertible Isocyanide for the Ugi Four-Component-Coupling Reaction
1-Hydroxy-2-methyl-2-propyl Isocyanide (HMPI) as a New Convertible Isocyanide for the Ugi Four-Component-Coupling Reaction
复制标题
1-羟基-2-甲基-2-丙基异氰化物 (HMPI) 作为 Ugi 四组分偶联反应的新型可转换异氰化物
DOI：
10.1055/s-0033-1338967
复制
发表时间：
2013
期刊：
影响因子：
2
通讯作者：
Yuichi Ishikawa
中科院分区：
文献类型：
--
作者：
Masato Oikawa;Yutaro Sugamata;Manami Chiba;Koichi Fukushima;Yuichi Ishikawa
Ugi反应是合成α-酰胺的一个有用的四组分偶联反应。然而，两种酰胺的选择性转化通常是困难的。在这里，我们报告1-羟基-2-甲基-2-丙基异氰化物（HMPI）作为一个新的成员的“可转换异氰化物”类用于解决这个问题。HMPI无臭，在Ugi反应中表现出良好的反应活性，生成N-（1-羟基-2-甲基-2-丙基）酰胺，后者在Zn（OTf）2介导的溶剂分解中顺利转化为酯。总体而言，通过使用HMPI，结构不同的α-氨基酸酯可通过两个步骤容易地获得。
The Ugi reaction is a useful four-component coupling reaction for α-(acylamino)amide. However, selective transformation of the two amides is generally difficult. Here, we report 1-hydroxy-2-methyl-2-propyl isocyanide (HMPI) as a new member of a ‘convertible isocyanide’ class used to solve the problem. HMPI is odorless and shows good reactivity in the Ugi reaction to giveN-(1-hydroxy-2-methyl-2-propyl) amides, which are smoothly converted into esters upon Zn(OTf)2-mediated solvolysis. Overall, structurally diverse α-amino acid esters are readily accessible in two steps by using HMPI.