多组分循环添加剂:维нилcyclopropanes,alkynes和CO的四组分 [5+1+2+1]循环添加剂
Paul A Wender1, Gabriel G Gamber, Robert D Hubbard
1Stanford University, Department of Chemistry, Stanford, California 94305-5080, USA. wenderp@stanford.edu
Journal of the American Chemical Society
|March 3, 2005
概括
研究人员开发了一种新型的四组分循环添加反应. 这种新方法可以有效地从乙烯基cyclopropanes,alkynes和一氧化碳合成氧化产品.
科学领域:
- 有机化学 有机化学
- 催化剂是一种催化剂.
- 合成方法论 合成方法论
背景情况:
- 过渡金属催化反应通常涉及反应性中间体.
- 之前的工作建立了三组件循环添加 ([5+2+1], [4+2+1], [2+2+1]).
研究的目的:
- 发现和开发新的循环添加反应.
- 探索具有多个组成部分的催化中间体的拦截.
- 为了合成复杂的氧胺结构.
主要方法:
- 开发一个四组分的 [5+1+2+1] 循环添加反应.
- 使用乙烯基cyclopropanes,alkynes和一氧化碳 (CO) 作为基板.
- 研究的基质范围,包括终端基因和替代的乙烯基cyclopropanes.
主要成果:
- 在良好的产量中成功合成了氧胺产品.
- 对和基替代终端基的证明耐受性.
- 在乙烯基cyclopropane前体上显示了可预测的替代模式.
- 使用二基基材实现双向反应,形成10个C-C键和4个环.
结论:
- 确定了一种新的四组分循环添加反应.
- 这种反应提供了一个简单而有效的途径,以取代氧.
- 通过多组分,双向反应进行复杂分子合成的潜力.
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Cycloalkanes are saturated cyclic hydrocarbons with carbon atoms arranged in the form of rings. They have two fewer hydrogen atoms than the corresponding acyclic alkane; therefore, their general formula is CnH2n. The structural formulas of cycloalkanes are simplified using the line-angle representation. The regular polygons are used to represent the cycloalkane rings, with each side representing a carbon-carbon bond.
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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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