铜催化异组选择性合的二甲基
Minjae Kim1, Bohyun Park2,3, Minkyeong Shin1
1Department of Chemistry, Pohang University of Science and Technology (POSTECH), Pohang 37673, Republic of Korea.
Journal of the American Chemical Society
|January 4, 2021
概括
这项研究引入了一种新型的铜催化反应,用于选择性合石二甲基. 这种方法有效地产生富含酸的酸,这些酸是有价值的基石.
科学领域:
- 有机化学
- 催化剂
- 合成化学
背景情况:
- 宝石二甲基是多功能合成中间体.
- 含化合物的酶选择性合成仍然具有挑战性.
研究的目的:
- 开发一种由铜催化,对宝石二甲基进行反选择性结合.
- 合成富含抗氧化物的同质酸.
主要方法:
- 铜化物催化反应
- 使用H8-BINOL衍生的胺联体.
- 使用化物作为化剂.
主要成果:
- 已经实现了 gem-diborylalkanes 的反选择性结合.
- 在良好的产量和高反比率下生成了各种丰富的同质酸.
- 确定了一种性α-玻里基铜中间体.
结论:
- 开发了一种有效的催化系统,用于酶选择性合成.
- 证明了宝石二甲基在制造性构建块中的实用性.
- 提供了对抗选择性转移过程的机制性见解.
相关概念视频
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation
3.7K
Catalytic hydrogenation of alkenes is a transition-metal catalyzed reduction of the double bond using molecular hydrogen to give alkanes. The mode of hydrogen addition follows syn stereochemistry.
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
The metal catalyst used can be either heterogeneous or homogeneous. When hydrogenation of an alkene generates a chiral center, a pair of enantiomeric products is expected to form. However, an enantiomeric excess of one of the products can be facilitated using an enantioselective reaction or an...
3.7K
Regioselectivity and Stereochemistry of Hydroboration
9.0K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn stereochemistry.
9.0K
α-Alkylation of Ketones via Enolate Ions
3.6K
Ketones with α protons are deprotonated by strong bases like lithium diisopropylamide (LDA) to form enolate ions. The anion is stabilized by resonance, and its hybrid structure exhibits negative charges on the carbonyl oxygen and the α carbon. This ambident nucleophile can attack an electrophile via two possible sites: the carbonyl oxygen, known as O-attack, or the α carbon, known as C-attack. The nucleophilic attack via the carbanionic site is preferred. This is due to the...
3.6K
Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation
8.5K
Introduction
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
Like alkenes, alkynes can be reduced to alkanes in the presence of transition metal catalysts such as Pt, Pd, or Ni. The reaction involves two sequential syn additions of hydrogen via a cis-alkene intermediate.
8.5K
Radical Substitution: Allylic Bromination
6.0K
In organic synthesis, the formation of products can be altered by changing the reaction conditions. For example, a dibromo addition product is formed when propene is treated with bromine at room temperature. In contrast, propene undergoes allylic substitution in non-polar solvents at high temperatures to give 3-bromopropene. In order to avoid the addition reaction, the bromine concentration must be kept as low as possible throughout the reaction. This can be achieved using N-bromosuccinimide...
6.0K
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide
11.8K
Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
11.8K


