通过金属基C-H基化来构建5个成员环结构的Enantioselective激素循环化
Yong Wang1, Xin Wen1, Xin Cui2
1Department of Chemistry, Merkert Chemistry Center , Boston College , Chestnut Hill , Massachusetts 02467 , United States.
Journal of the American Chemical Society
|March 28, 2018
概括
研究人员开发了一种新的催化方法,用于使用和的C-H键进行激进循环. 这种方法使得从简单的化物中能够对性罗利丁和其他五个成员环进行酶选择性合成.
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:
- 激素循环化对于合成环状结构至关重要.
- 传统方法需要不和基质,限制了它们的范围.
- 需要一个新的策略来利用现有的和C-H债券.
研究的目的:
- 开发一种使用和C-H基质进行激素循环的新型催化系统.
- 为了实现有价值的循环化合物的酶选择性合成.
- 为了建立一个新的回复合成方法,用于五个成员的环结构.
主要方法:
- 开发一种基于的催化剂系统.
- 催化激活亚利法性二化合物.
- 对于C(sp3) -H键的对抗选择性基质化.
主要成果:
- 能有效地构建性罗利丁和其他五个成员的循环化合物.
- 使用和基质,展示一种新的激素循环化方式.
- 成功结合C-H和C=O元素,形成C-C键.
结论:
- 开发的基于CO2的系统为传统的激进循环化提供了一个强大的替代方案.
- 这种方法提供了一种新的回合成范式,用于访问奇拉循环分子.
- 这种方法使得从简单的开链化物中合成有价值的五环环.
相关概念视频
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents
10.2K
In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
10.2K
Radical Substitution: Hydrogenolysis of Alkyl Halides with Tributyltin Hydride
2.3K
Radical substitution reactions can be used to remove functional groups from molecules. The hydrogenolysis of alkyl halides is one such reaction, where the weak Sn–H bond in tributyltin hydride reacts with alkyl halides to form alkanes. Here, the reagent Bu3SnH yields tributyltin halide as a byproduct.
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
The bonds formed in this reaction are stronger than the bonds broken, making it energetically favorable. The reaction follows a radical chain mechanism similar to radical halogenation reactions,...
2.3K
Radicals: Electronic Structure and Geometry
5.1K
This lesson delves into the geometry of a radical, which is influenced by the electronic structure of the molecule. The principle is similar to that of a lone pair, where the unpaired electron influences the geometry at the radical center.
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
Accordingly, the structure of a trivalent radical lies between the geometries of carbocations and carbanions. An sp2-hybridized carbocation is trigonal planar, while an sp3-hybridized carbanion is trigonal pyramidal. Here, the difference in geometry is...
5.1K
Five-Membered Heterocyclic Aromatic Compounds: Overview
5.6K
Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
5.6K
Alkyl Halides
20.1K
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
20.1K
5-Number Summary
5.7K
In a dataset, the 5-number summary includes the minimum data value, the data value of the first quartile, the median data value or data value of the second quartile, the data value of the third quartile, and the maximum data value. These 5 data values can be visualized as a box and whisker plot.
In a box plot, the minimum and maximum data values represent the lower and upper whiskers in the graph, and the median is designated as the center of the box in the chart. The first quartile and third...
In a box plot, the minimum and maximum data values represent the lower and upper whiskers in the graph, and the median is designated as the center of the box in the chart. The first quartile and third...
5.7K


