Formation of substituted 2-iminooxazolidines via intermolecular 1,2-addition/intramolecular N-vinylation using 3-substituted-2-bromo-2-propen-1-ols as substrates
Formation of substituted 2-iminooxazolidines via intermolecular 1,2-addition/intramolecular N-vinylation using 3-substituted-2-bromo-2-propen-1-ols as substrates
复制标题
DOI：
10.1016/j.tet.2018.08.051
复制
发表时间：
2018-11-01
期刊：
影响因子：
2.1
通讯作者：
Beifuss, Uwe
中科院分区：
文献类型：
--
作者：
Weischedel, Heike;Schmidt, Dietmar;Beifuss, Uwe
易得的3-取代-2-溴-2-丙烯-1-醇和二环己基碳二亚胺在100℃的二甲基亚砜中，以K3PO4为碱，在没有任何添加剂的情况下，在Cu2O催化下的等摩尔反应，可得到取代的2-亚氨基恶唑烷，产率高达80%。这种高选择性的转化被认为是从分子间的1，2-加成开始，然后是分子内的N-乙烯化。在没有Cu2O的情况下也可以获得产品，尽管产率较低。(C)2018爱思唯尔有限公司。保留所有权利。
The Cu2O-catalyzed reaction between equimolar amounts of easily available 3-substituted-2-bromo-2-propen-1-ols and dicyclohexyl carbodiimide in DMSO at 100 degrees C using K3PO4 as the base and in the absence of any additive exclusively delivers substituted 2-iminooxazolidines with yields up to 80%. The highly selective transformation is assumed to start with an intermolecular 1,2-addition, which is followed by an intramolecular N-vinylation. The products can also be obtained in the absence of Cu2O, albeit in lower yields. (C) 2018 Elsevier Ltd. All rights reserved.