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A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
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Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
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Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
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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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Prochirality

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The concept of prochirality leads to the nomenclature of the individual faces of a molecule and plays a crucial role in the enantioselective reaction. It is a concept where two or more achiral molecules react to produce chiral products. A typical process is the reaction of an achiral ketone to generate a chiral alcohol. Here, the achiral reactant reacts with an achiral reducing agent, sodium borohydride, to generate an equimolar mixture of the chiral enantiomers of the product. For example, an...
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Síntesis atroposelectiva de Si-CAryl activada por la funcionalidad de enlaces de los siloxanos de biarilo axialmente

Ming Wu1, Yi-Wei Chen1, Qian Lu1

  • 1Shenzhen Grubbs Institute, Department of Chemistry, Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology, Shenzhen 518055, China.

Journal of the American Chemical Society
|September 11, 2023
PubMed
Resumen
Este resumen es generado por máquina.

Este estudio introduce un método organocatalítico para la síntesis de los atropisómeros quirales de biarilo siloxano. El nuevo enfoque funciona eficientemente los enlaces silicio-carbono, ofreciendo una nueva ruta para crear valiosos compuestos quirales.

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Área de la Ciencia:

  • Química orgánica
  • Química del silicio orgánico
  • Catálisis asimétrica

Sus antecedentes:

  • Los organosilanos quirales son cruciales en la ciencia de los materiales, la catálisis y la medicina.
  • La síntesis tradicional de organosilanos quirales a menudo implica la catálisis de metales de transición para la funcionalización del enlace Si-C.

Objetivo del estudio:

  • Desarrollar un método organocatalítico eficiente para la síntesis atroposelectiva de los atropisómeros de siloxano de biarilo.
  • Para explorar la funcionalización de los enlaces silicio-carbono en los dináftosiloles utilizando nucleófilos de silanol.

Principales métodos:

  • Utilizó un catalizador de ácido Brønsted quiral recientemente desarrollado.
  • Se empleó una estrategia de funcionalización de enlaces Si-C organocatalíticos.
  • La reacción incluye protonación asimétrica y escisión / silanolisis simultánea de enlaces Si-C.

Principales resultados:

  • Se ha logrado una síntesis atroposelectiva eficiente de los atropisómeros de siloxano de biarilo.
  • Demostró la versatilidad del enlace Si-C para la derivatización en varios atropisómeros funcionales.
  • El método evita la dependencia de los catalizadores de metales de transición.

Conclusiones:

  • El método organocatalítico desarrollado proporciona una ruta eficiente a los siloxanos de biarilo axialmente quirales.
  • Este enfoque amplía la utilidad sintética de los organosilanos quirales y sus derivados.
  • Ofrece una alternativa libre de metales para sintetizar estructuras quirales complejas de siloxano.