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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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...
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Stereochemical Effects of Enolization01:12

Stereochemical Effects of Enolization

2.0K
The chiral α-carbon of the carbonyl compound is the stereocenter of the molecule. As shown in the figure below, when such a carbonyl compound undergoes racemization under an acidic or basic condition, an achiral enol is formed.
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Aldehydes and Ketones with Alcohols: Hemiacetal Formation01:19

Aldehydes and Ketones with Alcohols: Hemiacetal Formation

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Similar to water, alcohols can add to the carbonyl carbon of the aldehydes and ketones. The addition of one molecule of alcohol to the carbonyl compound forms the hemiacetal or half acetal. As depicted below, in a hemiacetal, the carbon is directly linked to an OH and OR group.
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Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration02:34

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
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Sharpless Epoxidation02:57

Sharpless Epoxidation

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The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
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Oxymercuration-Reduction of Alkenes02:36

Oxymercuration-Reduction of Alkenes

7.6K
Oxymercuration–reduction of alkenes is one of the major reactions converting alkenes to alcohols. It involves the hydration of alkenes with mercuric acetate in a mixture of tetrahydrofuran and water, forming an organomercury adduct. This is followed by a demercuration step in which the adduct is reduced to an alcohol using sodium borohydride.
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相关实验视频

Updated: Jul 12, 2025

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

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通过单一催化剂对酒精的脱血进行立体丰富的增强

Lu Wen1, Jia Ding1, Lingfei Duan1

  • 1State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China.

Science (New York, N.Y.)
|October 26, 2023
PubMed
概括

这项研究引入了一种光化学脱血方法,使用单一的性催化剂. 它通过多倍立体感应高效地丰富血清醇,克服了的挑战.

科学领域:

  • 有机化学
  • 摄影化学
  • 催化剂

背景情况:

  • 种族混合物的脱血面临着和可逆性的挑战.
  • 光化学方法提供了创新的途径,通常是通过C(sp3) -H结合的剥离.

研究的目的:

  • 开发一个光化学驱动的脱血协议.
  • 实现立体感应的倍增增强,以实现高立体选择性.

主要方法:

  • 使用单一的性催化剂进行C-C键裂变和形成.
  • 采用催化剂的连接物到金属的电荷转移激发.
  • 使用酸或比索克萨连体.

主要成果:

  • 通过邻近的完全替代的立体中心实现了高效的血糖醇丰富.
  • 达到了高达99:1的等离子比.
  • 机理学研究显示,通过一种前性中间体进行了连续的基因介导步骤.

结论:

  • 这项协议展示了一种新的方法,
  • 尽管单个步骤的选择性适度,但整体立体选择性很高.

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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Last Updated: Jul 12, 2025

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
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Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

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  • 光化学为立体化学丰富提供了强大的工具.