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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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Thermal and Photochemical Electrocyclic Reactions: Overview01:26

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Electrocyclic reactions are reversible reactions. They involve an intramolecular cyclization or ring-opening of a conjugated polyene. Shown below are two examples of electrocyclic reactions. In the first reaction, the formation of the cyclic product is favored. In contrast, in the second reaction, ring-opening is favored due to the high ring strain associated with cyclobutene formation.
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Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry01:29

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Woodward–Hoffmann Selection Rules and Microscopic Reversibility01:34

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Electrocyclic reactions, cycloadditions, and sigmatropic rearrangements are concerted pericyclic reactions that proceed via a cyclic transition state. These reactions are stereospecific and regioselective. The stereochemistry of the products depends on the symmetry characteristics of the interacting orbitals and the reaction conditions. Accordingly, pericyclic reactions are classified as either symmetry-allowed or symmetry-forbidden. Woodward and Hoffmann presented the selection criteria for...
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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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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
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Asymmetric Dearomatization/Cyclization Enables Access to Polycyclic Chemotypes.

Mikayo Hayashi1, Lauren E Brown2, John A Porco3

  • 1Department of Chemistry, Center for Molecular Discovery, Boston University, 590 Commonwealth Avenue, Boston, MA 02215 (USA).

European Journal of Organic Chemistry
|January 14, 2017
PubMed
Summary

Researchers created complex polycyclic molecules from simple precursors using enantioselective dearomatization. This method, aided by computational modeling, opens new pathways for synthesizing diverse chemical structures.

Keywords:
asymmetric catalysisdearomatizationphotocatalysispolycyclesradical reactions

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Computational Chemistry

Background:

  • Acylphloroglucinol derivatives are versatile starting materials.
  • Enantioselective synthesis of polycyclic compounds remains a challenge.

Purpose of the Study:

  • To develop a highly enantioselective dearomatization method for acylphloroglucinols.
  • To explore the utility of dearomatized products in subsequent transformations.
  • To elucidate the mechanism of enantioselectivity using computational methods.

Main Methods:

  • Enantioselective dearomatization catalyzed by a Trost ligand-palladium(0) complex.
  • Density Functional Theory (DFT) modeling to analyze reaction mechanisms and enantioselectivity.
  • Visible light-mediated photocycloadditions and oxidative free radical cyclizations.

Main Results:

  • Enantioenriched polycyclic compounds were successfully synthesized from an acylphloroglucinol scaffold.
  • A key reactant-ligand hydrogen bonding interaction was identified as crucial for enantioselectivity via DFT.
  • Novel polycyclic chemotypes, including tricyclo[4.3.1.01,4]decan-10-ones and substituted cycloheptanones, were accessed.

Conclusions:

  • The developed Trost ligand-palladium-catalyzed dearomatization offers a powerful route to enantioenriched polycyclic molecules.
  • Computational insights provide a mechanistic understanding of the observed enantioselectivity.
  • The dearomatized intermediates serve as versatile building blocks for constructing complex molecular architectures.