Formal [4+1] cycloaddition strategy for the synthesis of dihydrobenzofurans via Michael addition of 2-(2-nitrovinyl)-phenols and malonate esters (C1 synthon) and subsequent iodine-catalyzed oxidative annulation

作者：Leng, Jiaying; Meng, Jiang; Luo, Xiaoyan^*; Deng, Wei-Ping^*

来源：Tetrahedron, 2018, 74(49): 6993-6999.

DOI：10.1016/j.tet.2018.09.028

• Iodine-catalyzed
• Dihydrobenzofurans
• Nitroalkenes
• Malonate esters

A novel [4 +1] cycloaddition protocol for the synthesis of dihydrobenzo(naphtho)furan skeletons from readily available 2-(2-nitrovinyl)-phen(naphth)ols and malonate esters via a tandem Michael addition/iodine-catalyzed oxidative annulation has been developed. This method provides a new and facile application of malonate esters as 1,1-nucleophilicielectrophilic type C1 synthons without a pre-functionalization step and the plausible reaction mechanism is proposed.

• 出版日期2018-12-6
• 单位华东理工大学