一个实用的电友源,用于通过铜催化胺的合成基质氨基
Sheng Guo1, Jeffrey C Yang1, Stephen L Buchwald1
1Department of Chemistry , Massachusetts Institute of Technology , Cambridge , Massachusetts 02139 , United States.
Journal of the American Chemical Society
|October 30, 2018
概括
研究人员开发了一种新的铜催化方法,用于将初级氨基酸添加到和中. 这种实用方法利用1,2-糖作为一种新型的氨基源,使各种初级氨基的高效合成成为可能.
科学领域:
- 有机化学
- 合成化学
- 催化剂
背景情况:
- 氨基基组在和之间进行催化安装是一个重要的合成挑战.
- 使用氨的直接胺化通常需要恶劣的反应条件.
- 开发高效的电友氨基化试剂对于实际的氨基化方法至关重要.
研究的目的:
- 开发一种温和且实用的基和基的催化胺化方法.
- 引入1,2-糖作为一种新且有效的电友性初级氨基源.
- 合成多种主要氨基,包括性α分支和线性结构.
主要方法:
- 铜催化胺反应
- 使用1,2-糖作为电友性主要氨基源.
- 适用于广泛的和.
主要成果:
- 建立了对基和基的温和和一般协议.
- 该方法成功合成了各种性α分支初级氨基和线性初级氨基.
- 达到了抗逆转录病毒药物马拉维罗克的有效合成.
- 证明了其他药物的正式合成.
结论:
- 1,2-糖醇作为一种实用且有效的试剂,用于输送初级氨基群.
- 开发的铜催化方法提供了一种温和而多用途的初级氨基.
- 这种方法对药物和复杂有机分子的合成有重大影响.
相关概念视频
Chirality at Nitrogen, Phosphorus, and Sulfur
7.0K
Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
7.0K
Nomenclature of Primary Amines
4.5K
Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
4.5K
Preparation of 1° Amines: Gabriel Synthesis
4.6K
Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...
4.6K
Preparation of 1° Amines: Azide Synthesis
4.6K
Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
4.6K
Chirality
29.5K
Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...
29.5K
The Nitrogen Cycle
60.2K
Nitrogen atoms, present in all proteins and DNA, are recycled between abiotic and biotic components of the ecosystem. However, the primary form of nitrogen on Earth is nitrogen gas, which cannot be used by most animals and plants. Thus, nitrogen gas must first be converted into a usable form by nitrogen-fixing bacteria before it can be cycled through other living organisms. The use of nitrogen-containing fertilizers and animal waste products in human agriculture has greatly influenced the...
60.2K


