Han Jianlin, Li Tengfei, Pan Yi, Kattuboina Adiseshu, Li Guigen
School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, PR China.
Chem Biol Drug Des. 2008 Jan;71(1):71-7. doi: 10.1111/j.1747-0285.2007.00604.x. Epub 2007 Dec 7.
An efficient diamination reaction of alkenes has been developed for the synthesis of bromoalkyl-branched imidazolines by using CuI-PPh3 as the catalyst and N,N-dibromo-p-toluenesulfonamide as the nitrogen/halogen sources. A good scope of alkene substrates, including alpha,beta-unsaturated ketones, alpha,beta-unsaturated esters and simple olefins, was achieved for this reaction. Meanwhile, various nitriles were utilized as nucleophilic nitrogen sources. Modest to good yields and excellent regio- and stereoselectivity have been obtained. The stereochemistry was unambiguously confirmed by X-ray structural analysis. A new mild condition was found for the opening of resulting imidazolines by using SnCl4 as the promoter.
通过使用碘化亚铜-三苯基膦作为催化剂以及N,N-二溴对甲苯磺酰胺作为氮/卤素源，开发了一种用于合成溴代烷基支链咪唑啉的高效烯烃双胺化反应。该反应实现了包括α,β-不饱和酮、α,β-不饱和酯和简单烯烃在内的多种烯烃底物。同时，各种腈被用作亲核氮源。获得了中等至良好的产率以及优异的区域和立体选择性。通过X射线结构分析明确证实了立体化学。发现了一种使用四氯化锡作为促进剂来开环所得咪唑啉的新温和条件。
