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Related Concept Videos

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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...
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Heterogeneous Catalysis

Heterogeneous catalysis involves a catalyst in a different phase from the reactants. It is a process where the catalyst and the reactants are in distinct phases, typically solid and gas or liquid.Most heterogeneous catalysts are metals, metal oxides, or acids. The list includes transition metals like iron (Fe), cobalt (Co), nickel (Ni), palladium (Pd), platinum (Pt), chromium (Cr), manganese (Mn), tungsten (W), silver (Ag), and copper (Cu). These metals possess partially vacant d orbitals that...
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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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

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.
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

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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Regioselectivity and Stereochemistry of Hydroboration

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 stereochemistry.

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Low-loading asymmetric organocatalysis.

Francesco Giacalone1, Michelangelo Gruttadauria, Paola Agrigento

  • 1Dipartimento di Scienze e Tecnologie Molecolari e Biomolecolari (STEMBIO) Sez. Chimica Organica E. Paternò, Università di Palermo, Viale delle Scienze, Ed. 17, 90128, Palermo, Italy.

Chemical Society Reviews
|December 15, 2011
PubMed
Summary
This summary is machine-generated.

Chiral organocatalysts are revolutionizing asymmetric synthesis with high activity and stereoselectivity. This review highlights advances in low-loading organocatalysts across diverse catalytic fields.

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Area of Science:

  • Chemistry
  • Organic Synthesis
  • Catalysis

Background:

  • Asymmetric organocatalysis is a key pillar in modern asymmetric synthesis.
  • There is growing demand for highly active and stereoselective organocatalysts.
  • Low catalyst loading is crucial for efficient and sustainable chemical processes.

Purpose of the Study:

  • To critically review recent advances in chiral organocatalyst development.
  • To document organocatalysts used at ≤3 mol% loading.
  • To cover diverse sub-fields of asymmetric organocatalysis.

Main Methods:

  • Literature review of scientific publications.
  • Systematic documentation of chiral organocatalysts.
  • Analysis of catalyst loading and application scope.

Main Results:

  • Significant progress in developing highly active and stereoselective chiral organocatalysts.
  • Demonstration of systematic use of catalysts at ≤3 mol% loading.
  • Comprehensive coverage of aminocatalysis, Brønsted acid/base, Lewis acid/base, hydrogen bond, phase transfer, and N-heterocyclic carbene catalysis.

Conclusions:

  • Chiral organocatalysis is a rapidly advancing field with significant potential.
  • Low-loading organocatalysts are effective across a wide range of asymmetric transformations.
  • The reviewed catalysts represent the state-of-the-art in organocatalytic asymmetric synthesis.