Gold-catalysed synthesis of phosphonate-substituted oxetan-3-ones – an easy access to highly strained HWE reagents,Organic Chemistry Frontiers

当前位置： X-MOL 学术 › Org. Chem. Front. › 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.)

Gold-catalysed synthesis of phosphonate-substituted oxetan-3-ones – an easy access to highly strained HWE reagents
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2021-11-12 , DOI: 10.1039/d1qo01214b
Shaista Tahir ₁ , Jonas F. Wunsch ₁ , Matthias Rudolph ₁ , Frank Rominger ₁ , A. Stephen K. Hashmi _{1,

2}

Affiliation

A convenient approach for the attainment of strained phosphonate-substituted oxetan-3-ones, starting from easy to synthesise alkynyl phosphonates, is presented. With the aid of a pyridine-N-oxide, in a gold-catalysed step an α-oxo carbene species is generated as a key intermediate. After formal OH-insertion, synthetically useful HWE reagents can be attained. The synthetic utility of the obtained building blocks could be demonstrated, which yielded the 2-alkenyl oxetan-3-one scaffold in high yields after the HWE reaction.

中文翻译：

膦酸酯取代的氧杂环丁烷-3-酮的金催化合成——易于获得高度紧张的 HWE 试剂

介绍了一种从易于合成的炔基膦酸酯开始获得应变的膦酸酯取代的 oxetan-3-ones 的便捷方法。在吡啶-N-氧化物的帮助下，在金催化的步骤中，产生了作为关键中间体的α-氧代卡宾物种。在正式的 OH 插入后，可以获得合成有用的 HWE 试剂。可以证明所获得的构建块的合成效用，在 HWE 反应后以高产率产生了 2-alkenyl oxetan-3-one 支架。

更新日期：2021-12-01

点击分享查看原文

点击收藏

阅读更多本刊最新论文本刊介绍/投稿指南11