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Related Concept Videos

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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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...
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Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation02:24

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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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.
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

11.2K
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.
11.2K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

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The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
3.1K
Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

1.4K
The radical dimerization of ketones or aldehydes gives vicinal diols through a pinacol coupling reaction. However, the behavior of titanium metals used for the reaction as a source of electrons is unusual. When the reaction is carried out in the presence of titanium, diols can be isolated at low temperatures. Else titanium further reacts with diols, forming alkenes through the McMurry reaction.
1.4K
Reduction of Alkenes: Catalytic Hydrogenation02:13

Reduction of Alkenes: Catalytic Hydrogenation

12.5K
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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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Light mediated asymmetric approaches towards alkene difunctionalization.

Carolina Gimbert-Suriñach1, Roser Pleixats1, Albert Granados1

  • 1Departament de Química and Centro de Innovación en Química Avanzada (ORFEO-CINQA), Universitat Autònoma de Barcelona, Cerdanyola del Vallès, 08193 Barcelona, Spain. albert.granados@uab.es.

Organic & Biomolecular Chemistry
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Summary

Visible-light photochemistry enables asymmetric radical reactions for creating complex molecules. This review highlights advances in enantioselective alkene difunctionalization, focusing on strategies for stereocontrol in these sustainable transformations.

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Area of Science:

  • Organic Chemistry
  • Photochemistry
  • Asymmetric Synthesis

Background:

  • Visible-light photochemistry offers mild and sustainable conditions for chemical reactions.
  • Asymmetric difunctionalization of alkenes rapidly builds molecular complexity with optical activity.
  • Stereocontrol in light-driven radical reactions remains a significant challenge.

Purpose of the Study:

  • To review recent progress in light-mediated asymmetric alkene difunctionalization.
  • To emphasize strategies enabling efficient enantiocontrol in these reactions.
  • To provide a unified overview of current methods and future opportunities.

Main Methods:

  • Metallaphotoredox dual catalysis.
  • Bifunctional copper catalysts.
  • Use of enantioenriched reagents as traceless chiral auxiliaries.

Main Results:

  • Highlighting strategies for efficient enantiocontrol in light-driven alkene difunctionalization.
  • Discussing mechanistic aspects of radical generation, metal-radical interception, and enantioselective bond formation.
  • Showcasing advances in creating highly functionalized optically active organic skeletons.

Conclusions:

  • Visible-light photochemistry is a powerful tool for asymmetric radical transformations.
  • Significant progress has been made in enantioselective alkene difunctionalization.
  • Further development is needed for general, efficient, and sustainable asymmetric multicomponent reactions driven by visible light.