Cycloaddition reactions of enoldiazo compounds,Chemical Society Reviews

当前位置： X-MOL 学术 › Chem. Soc. Rev. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Cycloaddition reactions of enoldiazo compounds
Chemical Society Reviews ( IF 40.4 ) Pub Date : 2017-07-20 00:00:00 , DOI: 10.1039/c7cs00324b
Qing-Qing Cheng _{1,

2,

3,

4} , Yongming Deng _{1,

2,

3,

4} , Marianne Lankelma _{1,

2,

3,

4} , Michael P. Doyle _{1,

2,

3,

4}

Affiliation

Enoldiazo esters and amides have proven to be versatile reagents for cycloaddition reactions that allow highly efficient construction of various carbocycles and heterocycles. Their versatility is exemplified by (1) [2+n]-cycloadditions (n = 3, 4) by the enol silyl ether units of enoldiazo compounds with retention of the diazo functionality to furnish α-cyclic-α-diazo compounds that are themselves subject to further transformations of the diazo functional group; (2) [3+n]-cycloadditions (n = 1–5) by metallo-enolcarbenes formed by catalytic dinitrogen extrusion from enoldiazo compounds; (3) [2+n]-cycloadditions (n = 3, 4) by donor–acceptor cyclopropenes generated in situ from enoldiazo compounds that produce cyclopropane-fused ring systems. The role of dirhodium(II) and the emergence of copper(I) catalysts are described, as are the different outcomes of reactions initiated with these catalysts. This comprehensive review on cycloaddition reactions of enoldiazo compounds, with emphasis on methodology development, mechanistic insight, and catalyst-controlled chemodivergence, aims to provide inspiration for future discoveries in the field and to catalyze the application of enoldiazo reagents by the wider synthetic community.

中文翻译：

恩诺唑类化合物的环加成反应

恩诺地唑酯和酰胺已被证明是用于环加成反应的多功能试剂，可高效构建各种碳环和杂环。它们的多功能性由（1）Enoldiazozo化合物的烯醇甲硅烷基醚单元的[2+ n ]-环加成（n = 3，4）以及重氮官能团的保留来提供本身的α-环-α-重氮化合物来举例说明进行重氮官能团的进一步转化；（2）由烯醇二氮化合物催化二氮挤出形成的金属烯醇碳烯[3+ n ]-环加成（n = 1–5）；（3）原位产生的供体-受体环丙烯[2+ n ]-环加成（n = 3，4）由能产生环丙烷稠合环系统的烯丙唑类化合物制得。描述了（II）的作用和铜（I）催化剂的出现，以及用这些催化剂引发的反应的不同结果。这项对烯丙基ia唑化合物的环加成反应的全面综述，着重于方法学的发展，机理的洞察力以及催化剂控制的化学发散性，旨在为该领域的未来发现提供灵感，并催化更广泛的合成社区对烯丙基zo唑试剂的应用。

更新日期：2017-08-29

点击分享查看原文

点击收藏

公开下载

阅读更多本刊最新论文本刊介绍/投稿指南11