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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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[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Preparation and Reactions of Sulfides02:26

Preparation and Reactions of Sulfides

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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
6.0K
Reduction of Alkenes: Asymmetric Catalytic Hydrogenation02:17

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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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Hydroboration-Oxidation of Alkenes03:08

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In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
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Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism01:26

Preparation of 1° Amines: Hofmann and Curtius Rearrangement Mechanism

4.3K
The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...
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Asymmetric 1,3-Dioxane Synthesis by Using Bifunctional Thiourea Catalysis.

Yusuke Ono1, Akira Matsumoto2, Sho Shimozawa1

  • 1Institute For Catalysis, Hokkaido University, Sapporo, Hokkaido, Japan.

Chemistry, an Asian Journal
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Summary

This study introduces a new catalytic asymmetric reaction for synthesizing optically active 1,3-diols. The novel method efficiently converts readily available starting materials into valuable pharmaceutical building blocks.

Keywords:
1,3‐dioxanebifunctional thiourea catalystenantioselective synthesistrifluoromethyl ketoneα,β‐unsaturated carboxylic acid derivative

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Area of Science:

  • Organic Chemistry
  • Asymmetric Synthesis
  • Catalysis

Background:

  • The hemiacetalization/oxy-Michael addition cascade is effective for synthesizing 1,3-dioxanes and optically active 1,3-diols, crucial in pharmaceuticals.
  • Catalytic enantioselective reactions using carboxylic acid derivatives as Michael acceptors were previously unreported.

Purpose of the Study:

  • To develop a catalytic asymmetric hemiketalization/oxy-Michael addition cascade reaction.
  • To utilize phenyl trifluoromethyl ketone and chiral bifunctional thiourea catalysts.
  • To expand the scope to include carboxylic acid derivatives as Michael acceptors.

Main Methods:

  • Employing chiral bifunctional thiourea catalysts for asymmetric catalysis.
  • Utilizing phenyl trifluoromethyl ketone as the carbonyl reagent.
  • Investigating the cascade reaction with δ-hydroxy-α,β-unsaturated ketones and carboxylic acid derivatives.

Main Results:

  • Achieved good yields with high enantio- and diastereoselectivity.
  • Demonstrated applicability to both ketone and carboxylic acid derivative substrates.
  • Established a flexible synthetic route for compounds with high oxidation states.

Conclusions:

  • Developed a novel catalytic asymmetric hemiketalization/oxy-Michael addition cascade.
  • Successfully employed chiral bifunctional thiourea catalysts for high selectivity.
  • Expanded the synthetic utility to carboxylic acid derivatives, offering greater flexibility.