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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

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Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
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Regioselectivity of Electrophilic Additions-Peroxide Effect02:35

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In the presence of organic peroxides, the addition of hydrogen bromide to an alkene yields the isomer that is not predicted by Markovnikov’s rule. For example, the addition of hydrogen bromide to 2-methylpropene in the presence of peroxides gives 1-bromo-2-methylpropane. This addition reaction proceeds via a free radical mechanism, which reverses the regioselectivity. The free radical reaction mechanism involves three stages: initiation, propagation, and termination.
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[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement01:24

[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement

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The Claisen rearrangement is a [3,3] sigmatropic rearrangement of allyl vinyl ethers to unsaturated carbonyl compounds. The rearrangement is a concerted pericyclic reaction proceeding via a chair-like transition state.
2.9K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

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The stereochemistry of electrocyclic reactions is strongly influenced by the orbital symmetry of the polyene HOMO. Under thermal conditions, the reaction proceeds via the ground-state HOMO.
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
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Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction01:22

Alkenes via Reductive Coupling of Aldehydes or Ketones: McMurry Reaction

2.4K
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.
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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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Chemoselective Preparation of 1-Iodoalkynes, 1,2-Diiodoalkenes, and 1,1,2-Triiodoalkenes Based on the Oxidative Iodination of Terminal Alkynes
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Enantioselective Iridium-Catalyzed Allylic Cyclizations.

Michael A Schafroth1, Stephan M Rummelt1, David Sarlah1

  • 1ETH Zürich , Vladimir-Prelog-Weg 3, 8093 Zürich, Switzerland.

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Summary

This study introduces a new enantioselective synthesis method for complex ring systems using iridium catalysis and Lewis acids. The approach yields diverse structures with high stereocontrol, demonstrated in natural product synthesis.

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • Enantioselective synthesis is crucial for pharmaceuticals and natural products.
  • Developing efficient catalytic methods for complex ring systems remains a challenge.

Purpose of the Study:

  • To develop a novel method for enantioselective synthesis of carbo- and heterocyclic ring systems.
  • To utilize Lewis acid activation combined with iridium-catalyzed allylic substitution.

Main Methods:

  • Employing branched allylic alcohols and various carbon/heteronucleophiles.
  • Utilizing a combination of Lewis acid activation and iridium catalysis.
  • Investigating the scope and limitations of the developed reaction.

Main Results:

  • Achieved enantioselective synthesis of diverse carbo- and heterocyclic ring systems.
  • Obtained good yields and high enantioselectivities in the reactions.
  • Demonstrated the method's utility through asymmetric synthesis of erythrococcamides A and B.

Conclusions:

  • The described method offers a powerful new route for enantioselective synthesis.
  • The combined Lewis acid and iridium catalysis approach is effective for constructing complex ring systems.
  • This methodology has significant potential for synthesizing biologically active molecules.