Related Experiment Video
Updated: Dec 25, 2025
09:14
Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine
Published on: February 16, 2018
12.5K
Oxidative Kinetic Resolution of Acyclic Amines Based on Equilibrium Control
Kodai Saito1,2, Hiromitsu Miyashita1, Yui Ito3
1Department of Chemistry, Faculty of Science, Gakushuin University, 1-5-1 Mejiro, Toshima-ku, Tokyo 171-8588, Japan.
Organic Letters
|April 3, 2020
Summary
This study presents an oxidative kinetic resolution for racemic acyclic amines using imine derivatives and chiral phosphoric acid. The method achieves high yields and enantioselectivities by controlling reaction equilibrium.
Area of Science:
- Organic Chemistry
- Asymmetric Synthesis
Background:
- Racemic acyclic amines are common synthetic intermediates.
- Efficient methods for enantioselective synthesis are crucial in pharmaceuticals and fine chemicals.
Purpose of the Study:
- To develop a novel oxidative kinetic resolution for racemic acyclic amines.
- To achieve high yields and enantioselectivities using readily available reagents.
Main Methods:
- Utilized an imine derivative as a resolving reagent.
- Employed chiral phosphoric acid as a catalyst.
- Controlled reaction equilibrium by adjusting the ratio of the resolving reagent.
Main Results:
- Successfully resolved racemic acyclic amines.
- Achieved good yields with high to excellent enantioselectivities.
- Observed unique enantiodivergence based on equilibrium displacement.
Conclusions:
- The developed oxidative kinetic resolution is effective for acyclic amines.
- Equilibrium control is key to achieving high enantioselectivity.
- The method offers a versatile approach to enantiomerically enriched amines.
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Related Concept Videos
01:19Amines to Amides: Acylation of Amines
3.3K
Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary...
3.3K
01:38Preparation of Amines: Reductive Amination of Aldehydes and Ketones
3.6K
Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.
3.6K
01:29Preparation of Amines: Reduction of Oximes and Nitro Compounds
4.5K
Oximes can be reduced to primary amines using catalytic hydrogenation, hydride reduction, or sodium metal reduction. The reduction of aliphatic and aromatic nitro compounds to primary amines takes place by either catalytic hydrogenation or by using active metals like Fe, Zn, and Sn in the presence of an acid.
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
Though catalytic hydrogenation can reduce nitrobenzenes, the reduction is nonselective in the presence of other functional groups. For instance, if nitrobenzene contains an aldehyde group,...
4.5K
02:01Alkynes to Carboxylic Acids: Oxidative Cleavage
6.6K
Alkynes undergo oxidative cleavage in the presence of oxidizing reagents like potassium permanganate and ozone. The triple bond — one σ bond and two π bonds — is completely cleaved, and the alkyne is oxidized to carboxylic acids. When warm and basic aqueous potassium permanganate is used as an oxidizing agent, alkynes are first converted to carboxylate salts via an unstable α-diketone intermediate. Further, a mild acid treatment protonates the carboxylate anions...
6.6K
01:26Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism
3.9K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
3.9K
01:15Oxidations of Aldehydes and Ketones to Carboxylic Acids
5.3K
Oxidation of aldehydes and ketones results in the formation of carboxylic acids. Aldehydes, bearing hydrogen next to the carbonyl group, are easily oxidized compared to ketones. This is because an aldehydic proton can easily be abstracted during oxidation.
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
Aldehydes readily undergo oxidation in strong oxidizing agents such as potassium permanganate and chromic acid. The oxidation can also be carried out using mild oxidizing agents such as silver oxide. In fact, aldehydes can be easily oxidized...
5.3K