Abstract
Because the renewed interest of β – lactams in organic and medicinal chemistry, research in this field continues in producing new appealing progresses. This review tries to call the attention on synthetic aspects related to the generation of the four-membered heterocyclic ring, published in the last few years, with special accent in stereoselective synthetic approaches. The compendium will cover methods for achieving diastereo- and enantioselectivity during [2+2] cycloadditions, with the Staudinger reaction still as the first choice method, but also important achievements have been published for the imine-enolate condensation, the carbonylative cycloaddition, and the Kinugasa reaction. Significant success was also obtained in the synthesis of innovative 2-azetidinones through the formation of a single bond. In this respect, the C3-C4 bond formation, through intramolecular cyclization of linear epoxy or halo derivatives, and the carbenoid C-H insertion are among the most effectively exploited procedures. In addition, the adaptation of most procedures to solid-phase methodologies has facilitated the generation of molecular diversity based on the β – lactam skeleton.
Keywords: β-lactams, 2-azetidinones, stereoselective synthesis, chiral auxiliaries, chiral catalysts, memory of chirality
Current Organic Synthesis
Title: An Update on the Synthesis of β-Lactams
Volume: 6 Issue: 3
Author(s): M. Teresa Aranda, Paula Perez-Faginas and Rosario Gonzalez-Muniz
Affiliation:
Keywords: β-lactams, 2-azetidinones, stereoselective synthesis, chiral auxiliaries, chiral catalysts, memory of chirality
Abstract: Because the renewed interest of β – lactams in organic and medicinal chemistry, research in this field continues in producing new appealing progresses. This review tries to call the attention on synthetic aspects related to the generation of the four-membered heterocyclic ring, published in the last few years, with special accent in stereoselective synthetic approaches. The compendium will cover methods for achieving diastereo- and enantioselectivity during [2+2] cycloadditions, with the Staudinger reaction still as the first choice method, but also important achievements have been published for the imine-enolate condensation, the carbonylative cycloaddition, and the Kinugasa reaction. Significant success was also obtained in the synthesis of innovative 2-azetidinones through the formation of a single bond. In this respect, the C3-C4 bond formation, through intramolecular cyclization of linear epoxy or halo derivatives, and the carbenoid C-H insertion are among the most effectively exploited procedures. In addition, the adaptation of most procedures to solid-phase methodologies has facilitated the generation of molecular diversity based on the β – lactam skeleton.
Export Options
About this article
Cite this article as:
Aranda Teresa M., Perez-Faginas Paula and Gonzalez-Muniz Rosario, An Update on the Synthesis of β-Lactams, Current Organic Synthesis 2009; 6 (3) . https://dx.doi.org/10.2174/157017909788921899
DOI https://dx.doi.org/10.2174/157017909788921899 |
Print ISSN 1570-1794 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-6271 |
Call for Papers in Thematic Issues
Exploring the Role of Chemical Graph Theory in Advancing Current Organic Synthesis
Organic synthesis is a fundamental discipline in chemistry, crucial for the creation of complex molecules with diverse applications in pharmaceuticals, materials science, and beyond. However, the process of designing efficient synthetic routes for target molecules remains challenging. Chemical graph theory, a branch of theoretical chemistry, offers powerful tools for understanding ...read more
Photoswitches for Molecular Recognition
This Special Issue would cover the hot topics on synthesis and chemical and photophysical characterization of new photoswitchable derivatives and their applications on molecular recognition of metabolites and biological active compounds, both in physiological medium and in living cells. Photoswitches are compounds that can change their conformation or properties in ...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
Related Articles
-
Reprogramming of B Cells into Regulatory Cells with Engineered Fusokines
Infectious Disorders - Drug Targets Insights into the Pathogenesis and Intervention of Atherosclerosis
Vascular Disease Prevention (Discontinued) Amyloidosis and Auto-Inflammatory Syndromes
Current Drug Targets - Inflammation & Allergy Preface
Current Rheumatology Reviews A “Cute” Desensitization of TRPV1
Current Pharmaceutical Biotechnology Low Level Laser Therapy [LLLT] in Inflammatory and Rheumatic Diseases:A Review of Therapeutic Mechanisms
Current Rheumatology Reviews Solid Lipid Nanoparticles and Nanostructured Lipid Carriers of Celecoxib for Topical Application - Preparation, Characterization and Drug Penetration Through Rat Skin
Current Nanoscience The Role of Physical Exercise and Omega-3 Fatty Acids in Depressive Illness in the Elderly
Current Neuropharmacology Early Post-Operative Neuroimaging After Surgery for Malignant Glioma
Current Medical Imaging Inflammatory and Neurodegenerative Pathways in Depression: A New Avenue for Antidepressant Development?
Current Medicinal Chemistry Eating Disorders in the Time of the COVID-19 Pandemic: A Perspective
Endocrine, Metabolic & Immune Disorders - Drug Targets Relationship between Health Costs and Inflammatory Profile in Public Health
Current Pharmaceutical Design Treatment of Type 1 Diabetic Patients with Glucagon-Like Peptide-1 (GLP-1) and GLP-1R Agonists
Current Diabetes Reviews Controlled Release Inhalable Polymeric Microspheres for Treatment of Pulmonary Arterial Hypertension
Current Pharmaceutical Design Alzheimer’s Disease and Molecular Chaperones: Current Knowledge and the Future of Chaperonotherapy
Current Pharmaceutical Design Human Tissue Kallikrein: A New Bullet for the Treatment of Ischemia
Current Pharmaceutical Design Therapeutic Implications of Immunoparalysis in Critically Ill Patients
Inflammation & Allergy - Drug Targets (Discontinued) Acknowledgements to the Reviewers:
Inflammation & Allergy - Drug Targets (Discontinued) The Role of Bacterial Superantigens in the Immune Response: From Biology to Cancer Treatment
Current Cancer Therapy Reviews Human Tuberculosis I. Epidemiology, Diagnosis and Pathogenetic Mechanisms
Current Medicinal Chemistry