Silver(I)-Catalyzed Atroposelective Desymmetrization of N-Arylmaleimide via 1,3-Dipolar Cycloaddition of Azomethine Ylides: Access to Octahydropyrrolo[3,4-c]pyrrole Derivatives.

作者: Liu HC, Tao HY, Cong H, Wang CJ
学科名称: 医学;海洋科学
成果类型: 期刊论文
数据来源: SCIE
发表日期: 2016
年卷期页: 2016,81,(9),3752-60
期刊名: 《The Journal of organic chemistry》 影响因子和分区 年份    影响因子    区号
2016    4.849        2区 2015    4.785        2区 2014    4.721        2区 2013    4.564        2区 2012    4.204        2区
英文摘要: A highly efficient Ag(I)-catalyzed atroposelective desymmetrization of N-(2-t-butylphenyl)maleimide via 1,3-dipolar cycloaddition of in situ generated azomethine ylides has been established successfully, affording a facile access to a series of biologically important and enantioenriched octahydropyrrolo[3,4-c]pyrrole derivatives in generally high yields (up to 99%) with excellent levels of diastereo-/enantioselectivities (up to 99% ee, >20:1 dr). Subsequent transformations led to fascinating 2H-pyrrole and polysubstituted pyrrole compounds without loss of stereoselectivity. The absolute configuration of the generated chiral axis has been unambiguously identified as (M) through single-crystal X-ray diffraction analysis. Furthermore, on the basis of the comprehensive experimental results and the absolute configuration of one of the cycloadducts, the origin of the stereoselectivity was proposed to be attributed to the steric congestion imposed by the bulky PPh2 group of the chiral ligand and the tert-butyl group of N-(2-t-butylphenyl)maleimide. The possible hydrogen bond interaction between the NH2 group of the chiral ligand and one of the carbonyl groups of N-(2-t-butylphenyl)maleimide is considered to facilitate stabilizing the transition state.
语言: United States
出版类型: Journal Article
作者地址: College of Chemistry, Molecular Sciences, Wuhan University , Wuhan, China , 430072. [1]
State Key Laboratory of Elemento-organic Chemistry, Nankai University , Tianjin, China , 300071. [2]
College of Chemistry, Molecular Sciences, Wuhan University , Wuhan, China , 430072. [3]
College of Chemistry, Molecular Sciences, Wuhan University , Wuhan, China , 430072. [4]
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