Base-mediated diastereoselective [4 + 3] annulation of in situ generated ortho-quinone methides with C,N-cyclic azomethine imines,Organic & Biomolecular Chemistry

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Base-mediated diastereoselective [4 + 3] annulation of in situ generated ortho-quinone methides with C,N-cyclic azomethine imines
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-08-29 00:00:00 , DOI: 10.1039/c7ob01783a
Jianfeng Xu _{1,

2,

3,

4} , Shiru Yuan _{1,

2,

3,

4} , Jingyi Peng _{1,

2,

3,

4} , Maozhong Miao _{1,

2,

3,

4} , Zhengkai Chen _{1,

2,

3,

4} , Hongjun Ren _{1,

2,

3,

4}

Affiliation

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.

中文翻译：

碱介导的原位产生的邻醌甲基化物与C，N环偶氮甲亚胺的非对映选择性[4 + 3]环化

公开了在温和的碱性反应条件下通过原位生成邻醌甲基化物（o -QMs）使2-（1-甲苯基烷基）苯酚与C，N-环偶氮甲亚胺有效的[4 + 3]环化反应，具有中等至良好收率和出色的非对映选择性的七元杂环化合物。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合理化出色的非对映选择性。

更新日期：2017-09-20

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