Video Experimental Relacionado

Updated: Jan 22, 2026

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

Nucleófilos de organotitanio en la reacción asimétrica de acoplamiento cruzado: síntesis estereoconvergente de

Andrii Varenikov¹, Mark Gandelman¹

¹Technion - Israel Institute of Technology , Technion City, Haifa 3200008 , Israel.

Journal of the American Chemical Society

|July 2, 2019

Resumen

Los reactivos de organotitanio permiten nuevas reacciones asimétricas de acoplamiento cruzado para crear moléculas orgánicas quirales. Este estudio introduce su uso en la síntesis de tioéteres trifluorometilados, valiosos en el descubrimiento de fármacos.

Área de la Ciencia:

Química orgánica
Catálisis
Química medicinal

Sus antecedentes:

La catálisis asimétrica es crucial para sintetizar compuestos orgánicos quirales.
Las reacciones de acoplamiento cruzado catalizadas por níquel son herramientas poderosas para la síntesis estereoselectiva.
Los reactivos de organotitanio no se han explorado previamente como nucleófilos en estas reacciones.

Objetivo del estudio:

Introducir especies de organotitanio como nuevos socios de acoplamiento nucleófilo en reacciones de acoplamiento cruzado asimétrico.
Desarrollar la primera síntesis catalítica asimétrica de tioéteres sustituidos por CF3.
Comparar la eficacia de los reactivos de organotitanio con las equivalentes tradicionales de organomagnesio y organozinco.

Principales métodos:

Utilizando la catálisis asimétrica de níquel para las reacciones de acoplamiento cruzado.
El uso de especies de organotitanio como nucleófilos.
Desarrollo de una reacción estereoconvergente para la síntesis de tioéter.

Principales resultados:

Demostró por primera vez el uso exitoso de especies de organotitanium en el acoplamiento cruzado asimétrico.
Logró la primera síntesis catalítica asimétrica de tioéteres sustituidos por trifluorometil (CF3).
Los reactivos de organotitanio mostraron propiedades beneficiosas en comparación con los reactivos de organomagnesio y organozinco.

Conclusiones:

Los reactivos organotitanios representan una nueva clase de nucleófilos para el acoplamiento cruzado asimétrico.
Esta metodología proporciona un acceso eficiente a los tioéteres fluorados enriquecidos con enantio.
Los compuestos sintetizados tienen potencial para desarrollar nuevos productos farmacéuticos y agroquímicos.

Más Videos Relacionados

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols

Published on: April 4, 2014

Videos de Conceptos Relacionados

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

Reactions of α-Halocarbonyl Compounds: Nucleophilic Substitution

Nucleophilic substitution in α-halocarbonyl compounds can be achieved via an SN2 pathway. The reaction in α-haloketones is generally carried out with less basic nucleophiles. The use of strong basic nucleophiles leads to the generation of α-haloenolate ions, which often participate in other side reactions.

Nucleophilic Substitution Reactions

Nucleophilic Substitution Reactions

Historical perspective
In 1896, the German chemist Paul Walden discovered that he could interconvert pure enantiomeric (+) and (-) malic acids through a series of reactions. This conversion suggested the involvement of optical inversion during the substitution reaction. Further, in 1930, Sir Christopher Ingold described for the first time two different forms of nucleophilic substitution reactions, which are known as SN1 (nucleophilic substitution unimolecular) and SN2 (nucleophilic substitution...

Synthesis and Decomposition Reactions

Synthesis and Decomposition Reactions

Synthesis and decomposition are two types of redox reactions. Synthesis means to make something, whereas decomposition means to break something. The reactions are accompanied by chemical and energy changes.

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

Synthesis of α-Substituted Carbonyl Compounds: The Stork Enamine Reaction

α-Substituted ketones or aldehydes can be synthesized from enamines by the Stork enamine reaction, named after its pioneer Gilbert Stork. Enamines are useful synthetic intermediates where the lone pair on nitrogen is in conjugation with the C=C bond. They resemble enolate ions, as the resonance forms of both species have a nucleophilic α carbon.

Coupled Reactions

Coupled Reactions

Cellular processes such as building and breaking down complex molecules occur through stepwise chemical reactions. Some of these chemical reactions are spontaneous and release energy, whereas others require energy to proceed. Cells often couple the energy-releasing reaction with the energy-requiring one to carry out important cell functions.
Energy in adenosine triphosphate or ATP molecules is easily accessible to do work. ATP powers the majority of energy-requiring cellular reactions....

Crossed Aldol Reactions: Overview

Crossed Aldol Reactions: Overview

Crossed aldol addition is the reaction between two different carbonyl compounds under acidic or basic conditions. Here, both the carbonyl compounds function as nucleophiles and electrophiles. As shown in Figure 1, such a reaction yields a mixture of products, two of which are formed via self-condensation, while the remaining two are formed via crossed-condensation. Without adjustment, the reaction's usefulness in organic chemistry is decreased.