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Updated: Nov 6, 2025
08:12
A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
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Extended Enolates: Versatile Intermediates for Asymmetric C-H Functionalization via Noncovalent Catalysis
Mikel Oiarbide1, Claudio Palomo1
1Departamento de Química Orgánica I, Universidad del País Vasco UPV/EHU, Manuel Lardizabal 3, 20018, San Sebastián, Spain.
Chemistry (Weinheim an Der Bergstrasse, Germany)
|May 7, 2021
Summary
This review explores catalyst-controlled organic synthesis of carbonyl compounds. It highlights advances in enantioselective reactions using noncovalent catalyst-enolate complexes, addressing regioselectivity challenges.
Area of Science:
- Organic synthesis
- Catalysis
- Stereoselective reactions
Background:
- Catalyst-controlled functionalization of carbonyl compounds is crucial in organic synthesis.
- Achieving high site- and stereoselectivity in these reactions is a key objective.
- Enantioselective transformations via noncovalent di(tri)enolate-catalyst complexes represent recent progress.
Purpose of the Study:
- To discuss challenges in controlling regioselectivity with ambifunctional di(tri)enolates.
- To review noncovalent activation approaches for carbonyl compound functionalization.
- To highlight advancements using metallic and metal-free catalysts.
Main Methods:
- Discussion of enantioselective transformations.
- Analysis of noncovalent di(tri)enolate-catalyst coordination species.
- Review of metallic and metal-free catalytic systems.
Main Results:
- Noncovalent activation enables control over functionalization of enolizable substrates.
- Strategies have been developed to manage regioselectivity issues with di(tri)enolates.
- Progress in achieving site- and stereoselectivity in carbonyl compound transformations.
Conclusions:
- Noncovalent activation strategies offer promising routes for selective carbonyl functionalization.
- Addressing regioselectivity remains a critical aspect in developing new catalytic methods.
- Advancements in both metallic and metal-free catalysts are expanding the scope of these reactions.
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