Video Experimental Relacionado

Updated: Feb 1, 2026

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Preparation of Enantiopure Non-Activated Aziridines and Synthesis of Biemamide B, D, and epiallo-Isomuscarine

Published on: June 13, 2022

La aziridinación estereospecífica de alquenos utilizando un amino-reactivo bifuncional: una reacción de

Joshua J Farndon¹, Tom A Young¹, John F Bower¹

¹School of Chemistry , University of Bristol , Bristol BS8 1TS , United Kingdom.

Journal of the American Chemical Society

|December 14, 2018

Resumen

La desprotección del ácido trifluoroacético (ATF) de las hidroxilaminas N-Boc activadas por O-T induce la aziridinación intramolecular. Esta reacción forma eficientemente complejos anillos N-heterocíclicos a través de un mecanismo estereospecífico, con potencial para aplicaciones intermoleculares.

Área de la Ciencia:

Química orgánica
Química sintética
Química Heterocíclica

Sus antecedentes:

Las hidroxilaminas N-Boc son productos intermedios sintéticos versátiles.
La activación de las hidroxilaminas es crucial para las reacciones posteriores.
Las reacciones intramoleculares ofrecen vías eficientes a estructuras complejas.

Objetivo del estudio:

Investigar la desprotección in situ de las hidroxilaminas N-Boc activadas por O-T.
Para explorar la formación de sistemas de anillos N-heterocíclicos a través de la aziridinación intramolecular.
Para aclarar el mecanismo de reacción y evaluar la viabilidad intermolecular.

Principales métodos:

Desprotección in situ mediante el uso de ácido trifluoroacético (ATF).
Síntesis de las hidroxilaminas N-Boc activadas por O-T con alquenos atados por N.
Estudios sintéticos y computacionales para determinar el mecanismo de reacción y la estereoquímica.

Principales resultados:

Aziridinación intramolecular exitosa de los alquenos atados a N.
Formación de complejos sistemas de anillos N-heterocíclicos.
Confirmación de un mecanismo de tipo aza-Prilezhaev específico para el diastereo.

Conclusiones:

La desprotección in situ proporciona una vía fácil para la aziridinación intramolecular.
La reacción es altamente estereoselectiva, produciendo andamios heterocíclicos complejos.
La metodología es prometedora para las reacciones de aziridinación intermolecular relacionadas.

Más Videos Relacionados

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

A Protocol for Safe Lithiation Reactions Using Organolithium Reagents

Published on: November 12, 2016

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Published on: February 16, 2018

Videos de Conceptos Relacionados

Amino acids

Amino acids

Amino acids are the monomers that comprise proteins. Each amino acid has the same fundamental structure, which consists of a central carbon atom, or the alpha (α) carbon, bonded to an amino group (NH2), a carboxyl group (COOH), and to a hydrogen atom. Every amino acid also has another atom or group of atoms bonded to the central atom known as the R group. There are 20 common amino acids present in proteins, each with a different R group. Variation in the amino acid sequence is responsible for...

Introduction to Electrophilic Addition Reactions of Alkenes

Introduction to Electrophilic Addition Reactions of Alkenes

The double bond in a simple, unconjugated alkene is a region of high electron density that can act as a weak base or a nucleophile. The filled π orbital (HOMO) of the double bond can interact with the empty LUMO of an electrophile. A bonding interaction occurs when the electrophile attacks between the two carbons; the electrophile then accepts a pair of electrons from the π bond and undergoes addition across the double bond, yielding a single product.
Addition and elimination...

Free-Radical Chain Reaction and Polymerization of Alkenes

Free-Radical Chain Reaction and Polymerization of Alkenes

The conversion of alkenes to macromolecules called polymers is a reaction of high commercial importance. The structure of the polymer is defined by a repeating unit, while the terminal groups are considered insignificant. The average degree of polymerization represents the number of repeating units in the polymer molecule and is denoted by the subscript n.

Polymer Classification: Stereospecificity

Polymer Classification: Stereospecificity

Polymerization generates chiral centers along the entire backbone of a polymer chain. Accordingly, the stereochemistry of the substituent group has a significant effect on polymer properties. Polymers formed from monosubstituted alkene monomers feature chiral carbons at every alternate position in the polymer backbone. Relative to the predominant orientation of substituents at the adjacent chiral carbons, the polymer can exist in three different configurations: isotactic, syndiotactic, and...

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

Aldehydes and Ketones to Alkenes: Wittig Reaction Mechanism

The Wittig reaction, which converts aldehydes or ketones to alkenes using phosphorus ylides, proceeds through a nucleophilic addition‒elimination process.
The reaction begins with the nucleophilic addition between a phosphorus ylide and the carbonyl compound. Due to its carbanionic character, phosphorus ylide acts as a strong nucleophile and attacks the electrophilic carbonyl group. This generates a charge-separated dipolar intermediate called betaine. The negatively charged oxygen atom and...

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

Aldehydes and Ketones to Alkenes: Wittig Reaction Overview

The Wittig reaction is the conversion of carbonyl compounds-aldehydes and ketones-to alkenes using phosphorus ylides, or the Wittig reagent. The reaction was pioneered by Prof. Georg Wittig, for which he was awarded the Nobel Prize in Chemistry.