Asymmetric Transfer Hydrogenation of Cyclic Imines in Water with a Versatile Hydrogen Donor Formic Acid/N-Methylpiperidine: Rapid Access to Highly Enantioselective Amines
CHEMISTRYSELECT(2016)
摘要
Asymmetric transfer hydrogenation (ATH) of cyclic imines in water has been investigated for the first time by using HCOOH in combination with bases other than triethylamine as H donor. Effect of FA/Base ratio has shown significant impact on activity and enantioselectivity for ATH reaction in water. Use of methanol as a co-solvent improved the reduction performance. FA/N-methylpiperidine was found to be excellent, versatile hydrogen donor for ATH of imine 6,7-dimethoxy-1-methyl-3,4-dihy-droisoquinoline (1a) giving by far the highest noted TOF value of 5940 h(-1). ATH of-different imines derivatives including 3, 4-dihydoisoquinolines, beta-carbolines and cyclic sulfonyl imines have been performed with excellent activity (91-99% yield) and enantioselectivity (88-97%) in very short time (1-2 min). This is very simple protocol for rapid access to enantioselective amines with very new and versatile hydrogen donor 1.1 FA/Nmethylpiperidine.
更多查看译文
关键词
Asymmetric,base,formic acid,hydrogenation,water
AI 理解论文
溯源树
样例
生成溯源树,研究论文发展脉络
Chat Paper
正在生成论文摘要