Abstract
Conjugate addition reactions of organometallic compounds to electron-poor olefins is a versatile synthetic methodology for the formation of new carbon–carbon bonds. However, a careful control of the regioselectivity of the process is needed because of the presence of two electrophilic sites in the activated olefin. This issue is often overcome by employing "soft" nucleophiles such as organocopper and organozinc reagents, because of their high selectivity towards the 1,4-addition. In contrast, organolithium compounds, which are "hard" nucleophiles, generally give access to 1,2-adducts, 1,4-conjugate addition being sometimes observed according to the nature of nucleophiles and/or electrophiles, or to the presence of additives. In this Minireview, we have described some peculiar examples to get an outline of the recent acquisitions in the field of the conjugate additions of functionalized organolithiums to electron-poor olefins. Particular attention is paid to the synthesis of complex structures starting from simple substrates by means of cascade reactions promoted by conjugate addition reactions with organolithiums.
Dedicated to the memory of Professor José Barluenga.Keywords: Organolithiums, conjugate addition, alkenes, heterocycles, stereoselectivity, cascade reactions.
Current Organic Chemistry
Title:Conjugate Additions of Organolithiums to Electron-poor Olefins: A Simple and Useful Approach to the Synthesis of Complex Molecules
Volume: 21 Issue: 3
Author(s): Paola Vitale, Vito Capriati, Saverio Florio, Filippo M. Perna and Antonio Salomone
Affiliation:
Keywords: Organolithiums, conjugate addition, alkenes, heterocycles, stereoselectivity, cascade reactions.
Abstract: Conjugate addition reactions of organometallic compounds to electron-poor olefins is a versatile synthetic methodology for the formation of new carbon–carbon bonds. However, a careful control of the regioselectivity of the process is needed because of the presence of two electrophilic sites in the activated olefin. This issue is often overcome by employing "soft" nucleophiles such as organocopper and organozinc reagents, because of their high selectivity towards the 1,4-addition. In contrast, organolithium compounds, which are "hard" nucleophiles, generally give access to 1,2-adducts, 1,4-conjugate addition being sometimes observed according to the nature of nucleophiles and/or electrophiles, or to the presence of additives. In this Minireview, we have described some peculiar examples to get an outline of the recent acquisitions in the field of the conjugate additions of functionalized organolithiums to electron-poor olefins. Particular attention is paid to the synthesis of complex structures starting from simple substrates by means of cascade reactions promoted by conjugate addition reactions with organolithiums.
Dedicated to the memory of Professor José Barluenga.Export Options
About this article
Cite this article as:
Vitale Paola, Capriati Vito, Florio Saverio, Perna M. Filippo and Salomone Antonio, Conjugate Additions of Organolithiums to Electron-poor Olefins: A Simple and Useful Approach to the Synthesis of Complex Molecules, Current Organic Chemistry 2017; 21 (3) . https://dx.doi.org/10.2174/1385272820666161021161644
DOI https://dx.doi.org/10.2174/1385272820666161021161644 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
Call for Papers in Thematic Issues
Advances of Heterocyclic Chemistry with Pesticide Activity
Global food safety and security will continue to be a global concern for the next 50 years and beyond. Plant diseases have had a significant impact on food safety and security throughout the entire food chain, from primary production to consumption. While conventional chemical pesticides have been traditionally used for ...read more
Calculation design of covalent/metal organic framework based catalysts
This research area combines theoretical computation and screening with machine learning for the design of covalent/metal organic framework-based catalysts, bridging the disciplines of organic chemistry, physical chemistry, computational chemistry, materials science, and machine learning. It covers several critical aspects: designing and synthesizing organic catalysts for improved performance, applying computational methods ...read more
Carbohydrates conversion in biofuels and bioproducts
Biomass pretreatment, hydrolysis, and saccharification of carbohydrates, and sugars bioconversion in biofuels and bioproducts within a biorefinery framework. Carbohydrates derived from woody biomass, agricultural wastes, algae, sewage sludge, or any other lignocellulosic feedstock are included in this issue. Simulation, techno-economic analysis, and life cycle analysis of a biorefinery process are ...read more
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
Related Journals
- Author Guidelines
- Graphical Abstracts
- Fabricating and Stating False Information
- Research Misconduct
- Post Publication Discussions and Corrections
- Publishing Ethics and Rectitude
- Increase Visibility of Your Article
- Archiving Policies
- Peer Review Workflow
- Order Your Article Before Print
- Promote Your Article
- Manuscript Transfer Facility
- Editorial Policies
- Allegations from Whistleblowers
- Announcements
Related Articles
-
Nanotechnology: A Promising Tool Towards Wound Healing
Current Pharmaceutical Design Patent Selections:
Recent Patents on Cardiovascular Drug Discovery Medical Treatment of Peripheral Arterial Disease: Current Concepts and Future Options
Vascular Disease Prevention (Discontinued) Cefepime and its Role in Pediatric Infections
Recent Patents on Anti-Infective Drug Discovery Small Molecules Antileishmanials: A Review
Letters in Drug Design & Discovery Patent Selections:
Recent Patents on Regenerative Medicine Consequences of Alcohol Consumption on Neurotransmitters -An Overview
Current Neurovascular Research Pharmacological Strategies to Overcome HER2 Cross-Talk and Trastuzumab Resistance
Current Medicinal Chemistry Mast Cell Stabilizers in the Treatment of Allergic Rhinitis
Anti-Inflammatory & Anti-Allergy Agents in Medicinal Chemistry Gender Differences in Graduate Bioentrepreneurship Education - A Case Study: University of San Francisco
Technology Transfer and Entrepreneurship (Discontinued) The Long Non-Coding RNAs in Neurodegenerative Diseases: Novel Mechanisms of Pathogenesis
Current Alzheimer Research Namitecan: a Hydrophilic Camptothecin with a Promising Preclinical Profile
Current Medicinal Chemistry MMP-9 Inhibitors in the Brain: Can Old Bullets Shoot New Targets?
Current Pharmaceutical Design Epigenetic Regulation of Cytochrome P450 Enzymes and Clinical Implication
Current Drug Metabolism Targeting Chemokine (C-X-C motif) Receptor 3 in Thyroid Autoimmunity
Recent Patents on Endocrine, Metabolic & Immune Drug Discovery Behavioral Experimental Paradigms for the Evaluation of Drug’s Influence on Cognitive Functions: Interpretation of Associative, Spatial/Nonspatial and Working Memory
CNS & Neurological Disorders - Drug Targets Beyond Rodent Models of Pain: Non-Human Primate Models for Evaluating Novel Analgesic Therapeutics and Elaborating Pain Mechanisms
CNS & Neurological Disorders - Drug Targets A Comprehensive Review on Exosomes and Microvesicles as Epigenetic Factors
Current Stem Cell Research & Therapy A New 4-phenyl-1,8-naphthyridine Derivative Affects Carcinoma Cell Proliferation by Impairing Cell Cycle Progression and Inducing Apoptosis
Anti-Cancer Agents in Medicinal Chemistry Nanocarriers for Systemic and Mucosal Vaccine Delivery
Recent Patents on Drug Delivery & Formulation