پیشرفت‌ها در سنتز آلی: جلد 12

Advances in Organic Synthesis is a book series devoted to the latest advances in synthetic approaches towards challenging structures. The series presents comprehensive reviews written by eminent authorities on different synthetic approaches to selected target molecules and new methods developed to achieve specific synthetic transformations or optimal product yields. Advances in Organic Synthesis is essential reading for all organic chemists in academia and the industry who wish to keep abreast of rapid and important developments in the field.This volume presents the following reviews:Stereoselective Methodologies for the Synthesis of Acyclic PolyisoprenoidsMonosubstituted Ferrocene-Containing Thermotropic Liquid CrystalsProgress in the Chemistry of PhosphorothioatesKinetic Resolution Using Diastereoselective Acylating Agents as a Synthetic Approach to Enantiopure AminesAdvances in the Synthesis of Functional α-Organyl gem-Bisphosphonates for Biomedical Applications. Cover Advances in Organic Synthesis: Volume 12 Copyright End User License Agreement Contents Preface List of Contributors 1. Stereoselective Methodologies for the Synthesis of Acyclic Polyisoprenoids Abstract Introduction Natural Head-to-Tail Polyisoprenoids Natural Tail-to-Tail Polyisoprenoids Syntheses of Head-to-tail Polyisoprenoids General ω-Functionalization of Short Natural Polyprenols Synthesis of Bifunctional Mono-Isoprenyl Building Blocks Synthesis of Bifunctional Polyisoprenyl Building Blocks Synthesis of Oligoprenoids by sp3-sp3 Carbon Bond Formation Construction of 1,5-Dienes via SN2 Reactions Construction of 1,5-Dienes via SN2’ Reactions Enzymatic and Biomimetic Approaches Synthesis of Polyisoprenoids by sp2-sp2 Carbon-Carbon Bond Formation Synthesis of Polyisoprenoids by Wittig Reaction Synthesis of Polyisoprenoids by Metathesis Reaction Synthesis of Polyisoprenoids by sp2-sp3 Carbon Bond Formation Miscellaneous Reactions [3,3] and [2, 3]-sigmatropic rearrangements [1.3]-Sigmatropic Rearrangements Synthesis of Z-Polyisoprenoids Syntheses of Tail-to-tail Polyisoprenoids: Squalene Functionalization of Squalene Synthetic Approaches to Squalene Functionalization of Carbocycles with Isoprenoid Side Chains: Isoprenoid Quinones Synthesis of Isoprenoid Quinones Arylation of Polyprenyl Chains via Electrophilic Aromatic Substitution Reactions Arylation of Polyprenyl Chains by Alkylation Reactions with Organolithium or Organomagnesium Derivatives Arylation of Polyprenyl Chains via Transition Metal Catalyzed Coupling Reactions Synthesis of Other Isoprenoid Substituted Carbocycles and Heterocycles Direct Alkylation Reactions Wittig Type Reactions Sigmatropic Rearrangements Organometallic-Catalyzed Cross-Coupling Reactions and New Organometallic Processes Polymerization Reactions Concluding Remarks Consent for Publication Acknowlegments Conflict of Interest References 2. Monosubstituted Ferrocene-Containing Thermo- tropic Liquid Crystals Abstract Introduction Liquid Crystalline Ferrocenes with Ferrocene Rigidly Connected to Mesogenic Unit and Flexible Alkyl Chain as Terminal Group Monosubstituted Liquid Crystalline Ferrocenes Containing A Cholesteryl Group Ferrocene Derivatives with Ferrocene Rigidly Connected to the Cholesteryl Unit Ferrocene Derivatives with Ferrocene Flexible Connected to Cholesteryl Unit Ferrocene Derivatives with Cholesterol Flexible Connected to Mesogenic Unit Symmetrical Derivatives with Two Monosubstituted Ferrocenyl Units Conclusions Consent for Publication Conflict of Interest Acknowlegments References 3. Progress in the Chemistry of Phosphorothioates Abstract Introduction Syntheses of Phosphorothioic Esters P-S Bond Formation from P-nucleophile and S-electrophile P-S Bond Formation from P-electrophile and S-nucleophile Metal-free Oxidative P-S Bond Formation Metal-catalyzed Processes Involving Phosphorus and Sulfur Sources Metal-catalyzed P-S Formation Metal-catalyzed Three-component Reactions From Phosphorothioic Acids or their Salts By S-alkylation By Metal-mediated C-S Bond Formation Reactions of Phosphorothioic Esters Rearrangement Reactions Anionic 1,2-Rearrangement Anionic 1,3-Rearrangement Anionic 1,4-Rearrangement Thiophosphate to Phosphoroamidate Rearrangement Anionic P-S Bond Cleavage with C-S Bond Formation Homolytic P-S Cleavage Metal-catalyzed P-S Cleavage; Thiophosphorylation of Triple Bonds Allylic Substitution of Phosphorothioate Group Conclusions Consent for Publication Conflict of Interest Acknowlegments References 4. Kinetic Resolution Using Diastereoselective Acylating Agents as a Synthetic Approach to Enantiopure Amines Abstract Introduction Basic Principles of Kinetic Resolution Acylative Kinetic Resolution of Racemic Amines Diasteroselective N-Acylation of Racemic Amines Early Examples Derivatives of 2-Arylpropionic Acids as Diastereoselective Acylating Agents Derivatives of 2-Hydroxy Carboxylic Acids as Diastereoselective Acylating Agents Amino Acid Derivatives as Diastereoselective Acylating Agents Concluding Remarks Consent for Publication Conflict of Interest Acknowlegments References 5. Advances in the Synthesis of Functional α-Organyl gem-Bisphosphonates for Biomedical Applications Abstract Introduction Synthesis from Phosphites and Monophosphonates via C-P Bond formation New Variations in the Michaelis-Arbuzov and Michaelis-Becker Reactions Phosphorylation of α-Anionic Monophosphonates Synthesis Via Enolate Chemistry Functionalization of Compounds Already Containing the P-C-P Backbone Alkylation of Methylenebisphosphonate Carbanions Synthesis Based on “Click” Methodology Radical Based Approach Miscellaneous Reactions Synthesis via Alkenylidene-1,1-bisphosphonates Addition Reactions Reactions with Organometallic Reagents Base-Promoted Addition of Carbon Nucleophiles Reactions with Alcohols, Thiols and Amines Reactions with Phosphorus Nucleophiles Cycloaddition reactions Concluding Remarks Consent for Publication Conflict of Interest Acknowlegments References Subject Index Cover back