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Photochemical Electrocyclic Reactions: Stereochemistry

Photochemical Electrocyclic Reactions: Stereochemistry

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

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

Reduction of Alkenes: Asymmetric Catalytic Hydrogenation

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...

Reduction of Alkenes: Catalytic Hydrogenation

Reduction of Alkenes: Catalytic Hydrogenation

Alkenes undergo reduction by the addition of molecular hydrogen to give alkanes. Because the process generally occurs in the presence of a transition-metal catalyst, the reaction is called catalytic hydrogenation.
Metals like palladium, platinum, and nickel are commonly used in their solid forms — fine powder on an inert surface. As these catalysts remain insoluble in the reaction mixture, they are referred to as heterogeneous catalysts.
The hydrogenation process takes place on the...

Thermal Electrocyclic Reactions: Stereochemistry

Thermal Electrocyclic Reactions: Stereochemistry

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.

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

Reduction of Alkynes to cis-Alkenes: Catalytic Hydrogenation

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.

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

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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Updated: Dec 14, 2025

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

Published on: May 21, 2019

Stereoinduction in Metallaphotoredox Catalysis.

Alexander Lipp¹, Shorouk O Badir¹, Gary A Molander¹

¹Department of Chemistry, Roy and Diana Vagelos Laboratories, University of Pennsylvania, 231 S. 34th Street, Philadelphia, PA, 19104-6323, USA.

Angewandte Chemie (International Ed. in English)

|July 18, 2020

Summary

This summary is machine-generated.

Metallaphotoredox catalysis enables mild synthesis of C(sp3)-hybridized centers. This review highlights recent advances in enantioselective nickel- and copper-catalyzed reactions for creating complex molecules.

Keywords:

cross-coupling energy transfer photocatalysis radical precursors stereoinduction

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[DPEPhosbcpCu]PF6: A General and Broadly Applicable Copper-Based Photoredox Catalyst

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Synthesis and Performance Evaluations of ZnCoS/ZnCdS with Twin Crystal Structure for Multifunctional Redox Photocatalysis in Energy Applications

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Published on: July 25, 2025

Area of Science:

Organic Chemistry
Catalysis
Synthetic Methodology

Background:

Metallaphotoredox catalysis is a powerful tool for forming C(sp3)-hybridized centers under mild conditions.
Transition-metal-catalyzed cross-couplings, particularly for C(sp2)-C(sp3) linkages, have expanded significantly with abundant radical precursors.
Understanding stereoinduction in dual catalytic processes is a key area of recent research.

Purpose of the Study:

To provide a critical overview of recent progress in enantioselective bond formations using nickel- and copper-catalyzed metallaphotoredox catalysis.
To discuss stereochemical control elements in diastereoselective transformations within this catalytic framework.

Main Methods:

Review of recent literature on nickel- and copper-catalyzed enantioselective and diastereoselective reactions.
Analysis of stereoinduction origins in dual catalytic systems.

Main Results:

Nickel and copper catalysis have been instrumental in exploiting metallaphotoredox catalysis for enantioselective bond formations.
Significant advancements have been made in controlling stereochemistry in these dual catalytic processes.

Conclusions:

Metallaphotoredox catalysis, particularly with Ni and Cu, offers mild and effective routes to stereodefined C(sp3) centers.
Continued investigation into stereochemical control elements will further expand the utility of these catalytic systems.