Xu Jianfeng, Yuan Shiru, Peng Jingyi, Miao Maozhong, Chen Zhengkai, Ren Hongjun
Department of Chemistry, Zhejiang Sci-Tech University, Hangzhou 310018, People's Republic of China.
Org Biomol Chem. 2017 Sep 20;15(36):7513-7517. doi: 10.1039/c7ob01783a.
An efficient [4 + 3] annulation of 2-(1-tosylalkyl)phenols with C,N-cyclic azomethine imines via in situ generation of ortho-quinone methides (o-QMs) under mild basic reaction conditions is disclosed, furnishing biologically interesting seven-membered heterocyclic compounds with moderate to good yields and excellent diastereoselectivities. A gram-scale reaction is performed to demonstrate the potential in industrial application and two transition states are proposed to rationalize the outstanding diastereoselectivity.
公开了一种在温和碱性反应条件下通过原位生成邻醌甲基化物（o-QMs）实现2-（1-对甲苯磺酰基烷基）苯酚与C，N-环状偶氮甲碱亚胺的高效[4 + 3]环化反应，以中等至良好的产率和优异的非对映选择性提供具有生物学意义的七元杂环化合物。进行了克级反应以证明其在工业应用中的潜力，并提出了两种过渡态以解释出色的非对映选择性。
