molecules ISSN by MDPI

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1 Molecules 2001, 6, molecules ISSN by MDPI Book Received* Organic Synthesis on Solid Phase. (Supports, Linkers, Reactions). By Zaragoza Dörwald, Florencio. Wiley-VCH, Weinheim, Pages: 474, Hardcover. Price: DM / EUR / SFR. ISBN Received: 1 December 2001 Organic synthesis on solid supports is a rapidly developing methodology, which offers several advantages if compared to traditional synthesis in solution. In recent years the number of substance classes that can be synthesised on solid phase has quickly increased, and solid-phase synthesis is becoming a valuable alternative to traditional synthesis - in particular when large numbers of different compounds in small quantities are needed for screening. This exhaustive and systematically organised reference work gives an in-depth view on organic syntheses on insoluble polymers from the basic principles to the newest developments. The work quickly guides the reader to any particular type of reaction and to the best method for preparing a given class of compounds on solid support. Many tables with clear preseantation collect valuable information about the feasibility of a given reaction on solid support, and a wealth of information is opened up to the reader through a thoroughly worked out and comprehensive reference list. This makes the book the first stop when it comes to synthesising your compounds on solid support. General Techniques and Analytical Tools for Solid-Phase Organic Synthesis Supports for Solid-Phase Organic Synthesis Linkers for Solid-Phase Organic Synthesis Preparation of Organometallic Compounds Preparation of Hydrocarbons

2 Molecules 2001, Preparation of Alkyl and Aryl Halides Preparation of Alcohols and Ethers Preparation of Sulfur Compounds Preparation of Organoselenium Compounds Preparation of Nitrogen Compounds Preparation of Phosphorus Compounds Preparation of Aldehydes and Ketones Preparation of Carboxylic Acid Derivatives Preparation of Carbonic Acid Derivatives Preparation of Heterocycles Preparation of Oligomeric Compounds Index Table of Contens: Glossary and Abbreviations XIV Experimental Procedures XX 1 General Techniques and Analytical Tools for Solid-Phase Organic Synthesis General Techniques for Performing Syntheses on Insoluble Supports Strategies for Parallel Synthesis Analytical Methods for Support-bound Intermediates Combustion Analysis Colorimetric Assays Infrared Spectroscopy Mass Spectrometry Nuclear Magnetic Resonance Spectroscopy Strategies for the Selection of Reactions and Reagents for Parallel Solid-Phase Synthesis 8 2 Supports for Solid-Phase Organic Synthesis Polystyrene Microporous Styrene--Divinylbenzene Copolymers Swelling Behavior Chemical Stability Functionalization Macroporous Styrene--Divinylbenzene Copolymers Miscellaneous Polystyrenes Poly(ethylene glycol)--polystyrene Graft Polymers Poly(ethylene glycol) Polyacrylamides Polyacrylamide--PEG Copolymers Silica Polysaccharides Miscellaneous Supports 27 3 Linkers for Solid-Phase Organic Synthesis Linkers for Carboxylic Acids Linkers for Acids Cleavable by Acids or Other Electrophiles Benzyl Alcohol Linkers Diarylmethanol (Benzhydrol) Linkers 37

3 Molecules 2001, Trityl Alcohol Linkers Non- Benzylic Alcohol Linkers Linkers for Acids Cleavable by Bases or Nucleophiles Benzyl Alcohol Linkers Non- Benzylic Alcohol Linkers Miscellaneous Linkers Cleavable by Bases or Nucleophiles Photocleavable Linkers for Carboxylic Acids Linkers for Acids Cleavable by Transition Metal Catalysis Linkers for Acids Cleavable by Enzymes Linkers for Thiocarboxylic Acids Linkers for Amides, Sulfonamides, Carbamates, and Ureas Benzylamine Linkers (Diarylmethyl)amine and Tritylamine Linkers Linkers for Amides Cleavable by Nucleophiles Nucleophilic Cleavage of Alkyl Esters Nucleophilic Cleavage of Aryl Esters Nucleophilic Cleavage of Oxime and Related Esters Nucleophilic Cleavage of Amides and Carbamates Linkers for Hydroxamic Acids and Hydrazides Linkers for Carboxylic Esters Linkers for Esters Cleavable by Nucleophiles Linkers for Lactones Cleavable by Electrophiles or Oxidants Linkers for Primary and Secondary Aliphatic Amines Benzylamine, (Diarylmethyl)amine, and Tritylamine Linkers Carbamate Attachment Miscellaneous Linkers for Aliphatic Amines Linkers for Tertiary Amines Linkers for Aryl- and Heteroarylamines Linkers for Guanidines and Amidines Linkers for Pyrroles, Imidazoles, Triazoles, and Tetrazoles Linkers for Alcohols and Phenols Attachment as Ethers Attachment as Silyl Ethers Attachment as Acetals Attachment as Esters Miscellaneous Linkers for Alcohols and Phenols Linkers for Thiols Linkers for Alkyl and Aryl Halides Linkers for Aldehydes and Ketones Attachment as Enol Ethers, Enamines, and Imines Attachment of Carbonyl Compounds as Acetals Miscellaneous Linkers for Aldehydes and Ketones Linkers for Olefins Linkers for Olefins Cleavable by b-elimination Linkers for Olefins Cleavable by Olefin Metathesis Linkers for Alkanes and Arenes 110

4 Molecules 2001, Cleavage followed by Decarboxylation Cleavage of Silanes and related Compounds Reductive Cleavage of Carbon--Oxygen and Carbon--Nitrogen Bonds Reductive Cleavage of Carbon--Phosphorus, Carbon--Sulfur, and Carbon--Selenium Bonds Non-Covalent Linkers Ion-Exchange Resins Transition Metal Complexes Miscellaneous Non-Covalent Linkers Preparation of Organometallic Compounds Group I and II Organometallic Compounds Group III Organometallic Compounds Group IV Organometallic Compounds Transition Metal Complexes Preparation of Hydrocarbons Preparation of Alkanes Preparation of Alkanes by Hydrolysis of Organometallic Compounds Preparation of Alkanes by Hydrogenation and Reduction Preparation of Alkanes by Carbon--Carbon Bond Formation Coupling Reactions with Group I Organometallic Compounds Coupling Reactions with Group II Organometallic Compounds Coupling Reactions with Boranes Coupling Reactions with Arylpalladium Compounds Alkylations with Alkyl Radicals Preparation of Cycloalkanes Preparation of Alkenes Preparation of Alkenes by b-elimination and Reduction Preparation of Alkenes by Carbonyl Olefination By Wittig Reaction By Aldol and Related Condensations By Other Carbonyl Olefinations Preparation of Alkenes by Olefin Metathesis Preparation of Alkenes by C-Vinylation Preparation of Cycloalkenes by Cycloaddition Preparation of Alkynes Preparation of Biaryls Preparation of Alkyl and Aryl Halides Preparation of Alkyl Halides Preparation of Aryl and Heteroaryl Halides Preparation of Alcohols and Ethers Preparation of Alcohols Reduction of Carbonyl Compounds Addition of Carbon Nucleophiles to C--O Double Bonds Miscellaneous Preparations of Alcohols Protective Groups for Alcohols Protective Groups Cleavable by Acids 193

5 Molecules 2001, Protective Groups Cleavable by Nucleophiles Preparation of Ethers Preparation of Dialkyl Ethers Preparation of Alkyl Aryl Ethers Preparation of Diaryl Ethers Preparation of Sulfur Compounds Preparation of Thiols Preparation of Thioethers Preparation of Sulfoxides and Sulfones Preparation of Sulfonamides Preparation of Sulfonic Esters Preparation of Organoselenium Compounds Preparation of Nitrogen Compounds Preparation of Amines Preparation of Amines by Aliphatic Nucleophilic Substitution With Support-Bound Alkylating Agents By Alkylation of Support-Bound Amines Preparation of Amines by Aromatic Nucleophilic Substitution With Support-Bound Arylating Agents By Arylation of Support-Bound Amines Preparation of Amines by Addition of Amines to C--C Double Bonds Preparation of Amines by Reduction of Imines Preparation of Amines by Reaction of Carbon Nucleophiles with Imines or Aminals Preparation of Amines by Reduction of Amides and Carbamates Preparation of Amines by Reduction of Nitro Compounds Preparation of Amines by Reduction of Azides Miscellaneous Preparations of Amines Protective Groups for Amines Carbamates Amides Cyclic Imides Enamines Imines N-Alkyl and N-Aryl Derivatives N-Sulfenyl and N-Sulfonyl Derivatives Preparation of Quaternary Ammonium Salts Preparation of Hydrazines and Hydroxylamines Preparation of Azides Preparation of Diazo Compounds Preparation of Nitro Compounds Preparation of Phosphorus Compounds Phosphonic Acid Derivatives Preparation of Aldehydes and Ketones Preparation of Aldehydes and Ketones by C-Acylation Preparation of Aldehydes and Ketones by Oxidation Miscellaneous Preparations of Aldehydes and Ketones 278

6 Molecules 2001, Preparation of Carboxylic Acid Derivatives Preparation of Amides Preparation of Amides by Acylation of Amines with Isolated Acylating Agents Acylation of Amines with Acylating Reagents Formed In Situ Activation of Acids with Carbodiimides Activation of Acids with Phosphonium Salts Activation of Acids with Uronium Salts Miscellaneous Preparations of Amides Preparation of Amides by C-Alkylation of Other Amides Preparation of Amides by N-Alkylation of Other Amides Preparation of Hydroxamic Acids and Hydrazides Preparation of Carboxylic Acids Preparation of Carboxylic Esters Preparation of Esters from Support-Bound Alcohols Esterification of Support-bound Alcohols with N-Protected a-amino Acids Preparation of Esters from Support-Bound Alkylating Agents Preparation of Esters from Support-Bound Carboxylic Acids Preparation of Esters by Chemical Modification of Other Esters Preparation of Thiol Esters Preparation of Amidines and Imino Ethers Preparation of Nitriles and Isonitriles Preparation of Imides Preparation of Thioamides Preparation of Carbonic Acid Derivatives Preparation of Carbodiimides Preparation of Isocyanates and Isothiocyanates Preparation of Guanidines Preparation of Ureas Preparation of Thioureas and Isothioureas Preparation of Carbamates Preparation of Carbonates and Miscellaneous Carbonic Acid Derivatives Preparation of Heterocycles Preparation of Epoxides and Aziridines Preparation of Azetidines and Thiazetidines Preparation of Pyrroles and Pyrrolidines Preparation of Indoles and Indolines Preparation of Furans and Tetrahydrofurans Preparation of Benzofurans and Dihydrobenzofurans Preparation of Thiophenes Preparation of Imidazoles Preparation of Hydantoins (2,4-Imidazolidinediones) and Thiohydantoins Preparation of Benzimidazoles Preparation of Isoxazoles Preparation of Oxazoles and Oxazolidines Preparation of Thiazoles and Thiazolidines Preparation of Pyrazoles 374

7 Molecules 2001, Preparation of Triazoles, Tetrazoles, Oxadiazoles, and Thiadiazoles Preparation of Pyridines and Dihydropyridines Preparation of Tetrahydropyridines and Piperidines Preparation of Fused Pyridines Preparation of Pyridazines (1,2-Diazines) Preparation of Pyrimidines (1,3-Diazines) Preparation of Quinazolines Preparation of Pyrazines and Piperazines (1,4-Diazines), and Fused Derivatives thereof Preparation of Diketopiperazines Preparation of Miscellaneous 1,4-Diazines and Quinoxalines Preparation of Triazines Preparation of Pyrans and Benzopyrans Preparation of Oxazines and Thiazines Preparation of Azepines and Larger Heterocycles with one Nitrogen Atom Preparation of Diazepines, Thiazepines, and larger Heterocycles with more than one Het eroatom Preparation of Oligomeric Compounds Peptides Merrifield\9s Peptide Synthesis The Boc Strategy The Fmoc Strategy Side-Chain Protection Backbone Protection Cyclic Peptides Oligonucleotides Historical Overview The Phosphotriester Method The Phosphoramidite and H-Phosphonate Methods Oligonucleotide Analogs Oligosaccharides Glycosylation with Glycosyl Bromides Glycosylation with Glycosyl Sulfoxides Glycosylation with Glycosyl Thioethers Glycosylation with Miscellaneous Glycosyl Donors Miscellaneous Oligomeric Compounds Oligoamides Oligoglycines Peptide Nucleic Acids (PNA) Oligoesters Oligoureas and Oligothioureas Oligocarbamates Oligosulfonamides Oligomeric Phosphoric Acid Derivatives Peptide-Derived Oligomeric Compounds Oligomers Prepared by C--C Bond Formation Dendrimers 441

8 Molecules 2001, Index 449 *Editor's Note: The brief summary and the contents of the books are reported as provided by the author or the publishers. Authors and publishers are encouraged to send review copies of their recent books of potential interest to readers of Molecules to the Editor-in-Chief (Dr. Shu-Kun Lin, MDPI, Saengergasse 25, CH-4054 Basel, Switzerland. Tel , Fax , molinfo@mdpi.org). Some books will be offered to the scholarly community for the purpose of preparing full-length reviews by MDPI (