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Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.

Preparation of 1° Amines: Azide Synthesis

Preparation of 1° Amines: Azide Synthesis

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...

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

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...

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview

In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.

Reduction of Alkenes: Catalytic Hydrogenation

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...

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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

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Published on: July 28, 2022

Recent Developments in Catalytic Asymmetric Aziridination.

Iurre Olaizola¹, Ana María Ochoa de Retana¹, Jesús M de Los Santos²

¹Department of Organic Chemistry I, Faculty of Pharmacy and Lascaray Research Center, University of the Basque Country (UPV/EHU), Paseo de La Universidad 7, 01006, Vitoria-Gasteiz, Spain.

Topics in Current Chemistry (Cham)

|September 9, 2025

Summary

This review covers recent advances in catalytic asymmetric aziridination, a key method for creating chiral amines and complex molecules. It highlights new techniques, their scope, limitations, and underlying mechanisms for organic synthesis applications.

Keywords:

2H-azirines Aza-Darzens Chiral aziridines Enantioselective aziridination Kinetic resolution

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Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles

Published on: August 22, 2018

Area of Science:

Organic Chemistry
Synthetic Chemistry

Background:

Aziridines are three-membered nitrogen-containing heterocycles, analogous to epoxides.
They are crucial intermediates in synthesizing chiral amines, complex molecules, and pharmaceutically relevant compounds.
Aziridines present significant synthetic challenges and opportunities in organic chemistry.

Purpose of the Study:

To provide a comprehensive overview of recent advancements in catalytic asymmetric aziridination.
To analyze novel methodologies, their scope, and limitations.
To offer mechanistic insights into these transformations.

Main Methods:

Review of recent literature on catalytic asymmetric aziridination.
Analysis of various synthetic methodologies and their applicability.
Discussion of mechanistic pathways involved in aziridination reactions.

Main Results:

Identification of novel catalytic systems and strategies for asymmetric aziridination.
Evaluation of the efficiency, selectivity, and substrate scope of different methods.
Elucidation of reaction mechanisms, aiding in the design of improved catalysts and protocols.

Conclusions:

Catalytic asymmetric aziridination is a rapidly evolving field with significant potential.
Continued development of novel methodologies is crucial for accessing complex chiral amines and molecules.
Mechanistic understanding is key to advancing the efficiency and applicability of aziridination reactions.