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姜耀甲教授和罗德平教授课题组在Chemical Communications发表研究论文
阅读次数:770 添加时间:2017/11/2 发布: 管理员

Directed C–C bond cleavage of a cyclopropane intermediate generated from N-tosylhydrazones and stable enaminones: expedient synthesis of functionalized 1,4-ketoaldehydes

Meiyan Ni,a Jianguo Zhang,a Xiaoyu Liang,a Yaojia Jiang*,a and Teck-Peng Loh*,ab

a Institute of Advanced Synthesis, School of Chemistry and Molecular Engineering, Jiangsu National Synergetic Innovation Center for Advanced Materials, Nanjing Tech University, Nanjing 211816, China

b Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637616, Singapore


Abstract: An efficient method to construct functionalized 1, 4-ketoaldehydes bearing all-carbon a-quaternary centers via regioseletive C-C bond activation has been described. Through cyclopropanation of bench-stable enaminones with in situ generated diazo reagents from N-tosylhydrazones, followed by selective C-C bond cleavage of the cyclopropane ring affords the 1, 4-ketoaldehyde derivatives in good to excellent yields. This method works with broad substrate scope and high regioseletivity.

Chem. Commun., 2017, in press (doi: 10.1039/C7CC07178G).  (2017年影响因子: 6.3).


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