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Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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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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Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
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In this lesson, the oxidation of alcohols is discussed in depth. The various reagents used for oxidation of primary and secondary alcohols are detailed, and their mechanism of action is provided.
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Sharpless Epoxidation02:57

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The conversion of allylic alcohols into epoxides using the chiral catalyst was discovered by K. Barry Sharpless and is known as Sharpless epoxidation. The use of a chiral catalyst enables the formation of one enantiomer of the product in excess. This chiral catalyst is mainly a chiral complex of titanium tetraisopropoxide and tartrate ester (specific stereoisomer). The stereoisomer used in the chiral catalyst dictates the formation of the enantiomer of the product. In other words, the use of...
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18.7K
Alkenes can be dihydroxylated using potassium permanganate. The method encompasses the reaction of an alkene with a cold, dilute solution of potassium permanganate under basic conditions to form a cis-diol along with a brown precipitate of manganese dioxide.
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SN2 Reaction: Stereochemistry02:23

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13.2K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
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Synthesis of Antiviral Tetrahydrocarbazole Derivatives by Photochemical and Acid-catalyzed C-H Functionalization via Intermediate Peroxides CHIPS
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Absolute asymmetric synthesis: protected substrate oxidation.

Susanne Olsson1, Per Martin Björemark, Theonitsa Kokoli

  • 1Department of Chemistry and Molecular Biology, University of Gothenburg, 412 96 Gothenburg (Sweden).

Chemistry (Weinheim an Der Bergstrasse, Germany)
|February 14, 2015
PubMed
Summary
This summary is machine-generated.

Researchers developed new ruthenium(II) complexes with chiral sulfide ligands. These complexes enable highly enantioselective oxidation of sulfides, yielding valuable chiral sulfoxides with over 98% enantiomeric excess.

Keywords:
asymmetric synthesiscrystal growthoxidationrutheniumsulfur ligands

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Area of Science:

  • Organometallic Chemistry
  • Asymmetric Synthesis
  • Coordination Chemistry

Background:

  • Ruthenium(II) complexes are versatile catalysts in organic synthesis.
  • Chiral sulfoxides are important intermediates in pharmaceuticals and materials science.
  • Developing efficient methods for enantioselective sulfide oxidation remains a key challenge.

Purpose of the Study:

  • To synthesize novel bidentate sulfide ligands coordinated by Ru(II) centers.
  • To achieve spontaneous resolution of these complexes for enantioselective synthesis.
  • To explore the enantioselective oxidation of sulfide ligands to chiral sulfoxides.

Main Methods:

  • Preparation and characterization of three new Ru(II)-sulfide conglomerates.
  • Spontaneous resolution via slow crystallization to obtain enantioenriched batches.
  • Enantioselective oxidation of sulfide ligands using the chiral complexes.
  • Characterization of stereoisomers using single-crystal X-ray diffraction, CD spectroscopy, and chiral HPLC.

Main Results:

  • Successful synthesis of three new Ru(II) complexes with bidentate sulfide ligands.
  • High enantiomeric excess (>98% ee) achieved in the oxidation of sulfide ligands to chiral sulfoxides.
  • Complete characterization of all relevant stereoisomers.
  • Demonstration of spontaneous resolution for generating enantioenriched crystal batches.

Conclusions:

  • The developed Ru(II) complexes are effective for enantioselective oxidation of sulfide ligands.
  • Spontaneous resolution provides a viable route to highly enantioenriched complexes.
  • Extending the ligand scope to monodentate sulfides could enable large-scale, recyclable enantioselective oxidation processes.