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Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

3.3K
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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Photochemical Electrocyclic Reactions: Stereochemistry01:26

Photochemical Electrocyclic Reactions: Stereochemistry

2.2K
The absorption of UV–visible light by conjugated systems causes the promotion of an electron from the ground state to the excited state. Consequently, photochemical electrocyclic reactions proceed via the excited-state HOMO rather than the ground-state HOMO. Since the ground- and excited-state HOMOs have different symmetries, the stereochemical outcome of electrocyclic reactions depends on the mode of activation; i.e., thermal or photochemical.
Selection Rules: Photochemical Activation
2.2K
Thermal and Photochemical Electrocyclic Reactions: Overview01:26

Thermal and Photochemical Electrocyclic Reactions: Overview

2.9K
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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Cycloaddition Reactions: MO Requirements for Photochemical Activation01:12

Cycloaddition Reactions: MO Requirements for Photochemical Activation

2.5K
Some cycloaddition reactions are activated by heat, while others are initiated by light. For example, a [2 + 2] cycloaddition between two ethylene molecules occurs only in the presence of light. It is photochemically allowed but thermally forbidden.
2.5K
Thermal Electrocyclic Reactions: Stereochemistry01:17

Thermal Electrocyclic Reactions: Stereochemistry

2.5K
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.
2.5K
Pericyclic Reactions: Introduction01:17

Pericyclic Reactions: Introduction

9.6K
Pericyclic reactions are organic reactions that occur via a concerted mechanism without generating any intermediates. The reactions proceed through the movement of electrons in a closed loop to form a cyclic transition state, where rearrangement of the σ and π bonds yields specific products.
Pericyclic reactions can be classified into three categories: electrocyclic reactions, cycloaddition reactions, and sigmatropic rearrangements. Electrocyclic reactions and sigmatropic...
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of &#945;-Imino &#947;-Lactones and Alkylidene Pyrazolones
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Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones

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Photoinduced Spirocyclization for the Synthesis of Spirocyclic Compounds.

Yu-Jie Cao1, Min Gu1, Quan-Qing Zhao1

  • 1Jiangsu Key Laboratory of Marine Pharmaceutical Compound Screening, College of Pharmacy, Jiangsu Ocean University, Lianyungang, China.

Chemistry (Weinheim an Der Bergstrasse, Germany)
|December 29, 2025
PubMed
Summary
This summary is machine-generated.

Visible-light photocatalysis enables efficient synthesis of spirocycles, crucial 3D scaffolds in pharmaceuticals. This review covers recent catalytic methods, substrate scope, and mechanisms for constructing these complex molecules.

Keywords:
cycloadditiondearomatizationradical spirocyclizationspirocyclesvisible light photocatalysis

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Area of Science:

  • Organic Chemistry
  • Photocatalysis
  • Medicinal Chemistry

Background:

  • Spirocycles are vital 3D structural motifs found in numerous natural products and pharmaceutical agents.
  • Their unique conformational and physicochemical properties make them attractive targets for drug discovery.
  • The synthesis of spirocyclic compounds has garnered significant research interest in the past decade.

Purpose of the Study:

  • To provide a comprehensive overview of recent advancements in visible-light-induced spirocyclization reactions.
  • To highlight key catalytic methodologies, substrate scope, and mechanistic insights in spirocycle synthesis.
  • To identify current limitations and future research opportunities in the field of photocatalytic spirocyclization.

Main Methods:

  • Review of literature focusing on visible-light photocatalysis for spirocyclization.
  • Analysis of catalytic systems, including photocatalysts and reaction conditions.
  • Examination of diverse substrate scopes and reaction mechanisms.

Main Results:

  • Detailed summary of state-of-the-art visible-light-mediated spirocyclization strategies.
  • Illustrative examples showcasing the efficiency and versatility of photocatalytic methods.
  • Discussion on the mechanistic pathways governing these transformations.

Conclusions:

  • Visible-light photocatalysis offers a powerful and sustainable approach for spirocycle synthesis.
  • Challenges remain in expanding substrate scope and catalyst efficiency.
  • Future research should focus on developing novel catalytic systems and exploring new synthetic applications.