Fragmentation of carbohydrate anomeric alkoxy radicals:: a new synthesis of chiral 1-halo-1-bromo compounds
Fragmentation of carbohydrate anomeric alkoxy radicals:: a new synthesis of chiral 1-halo-1-bromo compounds
复制标题
DOI：
10.1016/s0040-4039(03)01399-6
复制
发表时间：
2003-08-11
影响因子：
1.8
通讯作者：
Suárez, E
中科院分区：
文献类型：
--
作者：
González, CC;León, EI;Suárez, E
在溴存在下，由易得的碳水化合物衍生的1，2-卤代醇与二乙酰氧基碘代苯（DIB）反应，可温和地合成比原碳水化合物少一个碳原子的1-脱氧-1-卤代-1-溴代糖醇。该反应经历中间体异头烷氧基自由基的β-断裂。这些1-卤-1-溴多羟基化合物可能是有机合成中有价值的合成中间体。(C)2003 Elsevier Ltd.保留所有权利。
The reaction of 1,2-halohydrins derived from easily available carbohydrates with (diacetoxyiodo)benzene (DIB) in the presence of bromine is a mild procedure for the synthesis of 1-deoxy-1-halo-1-bromo-alditols with one carbon less than the original carbohydrate. The reaction goes through beta-fragmentation of the intermediate anomeric alkoxyl radicals. These 1-halo-1-bromo polyhydroxy compounds may be valuable synthetic intermediates in organic synthesis. (C) 2003 Elsevier Ltd. All rights reserved.