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Science of Synthesis: Houben-Weyl Methods of Molecular Transformations is the entirely new edition of the acclaimed reference series Houben-Weyl, the standard synthetic chemistry resource since 1909. This new edition is published in English and will comprise 48 volumes published between the years 2000 and 2008.
Science of Synthesis is a quality reference work developed by a highly esteemed editorial board to provide a comprehensive and critical selection of reliable organic and organometallic synthetic methods. This unique resource is designed to be the first point of reference when searching for a synthesis strategy.
For full information on the Science of Synthesis series, visit the Science of Synthesis Homepage
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Science of Synthesis is the authoritative and comprehensive reference work for the entire field of organic and organometallic synthesis.
Science of Synthesis presents the important synthetic methods for all classes of compounds and includes:
Methods critically evaluated by leading scientists
Background information and detailed experimental procedures
Schemes and tables which illustrate the reaction scope
As our understanding of the natural world increases, we begin to understand complex phenomena at molecular levels. This level of understanding allows for the design of molecular entities for functions ranging from material science to biology. Such design requires synthesis and, as the structures increase in complexity as a necessity for specificity, puts increasing demands on the level of sophistication of the synthetic methods. Such needs stimulate the improvement of existing methods and, more importantly, the development of new methods. As scientists confront the synthetic problems posed by the molecular targets, they require access to a source of reliable synthetic information. Thus, the need for a new, comprehensive, and critical treatment of synthetic chemistry has become apparent. To meet this challenge, an entirely new edition of the esteemed reference work Houben–Weyl Methods of Organic Chemistry will be published starting in the year 2000.
To reflect the new broader need and focus, this new edition has a new title, Science of Synthesis, Houben–Weyl Methods of Molecular Transformations. Science of Synthesis will benefit from more than 90 years of experience and will continue the tradition of excellence in publishing synthetic chemistry reference works. Science of Synthesis will be a balanced and critical reference work produced by the collaborative efforts of chemists, from both industry and academia, selected by the editorial board. All published results from journals, books, and patent literature from the early 1800s until the year of publication will be considered by our authors, who are among the leading experts in their field. The 48 volumes of Science of Synthesis will provide chemists with the most reliable methods to solve their synthesis problems. Science of Synthesis will be updated periodically and will become a prime source of information for chemists in the 21st century.
Science of Synthesis will be organized in a logical hierarchical system based on the target molecule to be synthesized. The critical coverage of methods will be supported by information intended to help the user choose the most suitable method for their application, thus providing a strong foundation from which to develop a successful synthetic route. Within each category of product, illuminating background information such as history, nomenclature, structure, stability, reactivity, properties, safety, and environmental aspects will be discussed along with a detailed selection of reliable methods. Each method and variation will be accompanied by reaction schemes, tables of examples, experimental procedures, and a background discussion of the scope and limitations of the reaction described.
The policy of the editorial board is to make Science of Synthesis the ultimate tool for the synthetic chemist in the 21st century.
We would like to thank all of our authors for submitting contributions of such outstanding quality, and, also for the dedication and commitment they have shown throughout the entire editorial process.
October 2000
The Editorial Board
D. Bellus (Basel, Switzerland)
E. N. Jacobsen (Cambridge, USA)
S. V. Ley (Cambridge, UK)
R. Noyori (Nagoya, Japan)
M. Regitz (Kaiserslautern, Germany)
P. J. Reider (New Jersey, USA)
E. Schaumann (Clausthal-Zellerfeld, Germany)
I. Shinkai (Tsukuba, Japan)
E. J. Thomas (Manchester, UK)
B. M. Trost (Stanford, USA)
Preface
Table of Contents
Introduction
C. J. Forsyth
37.1 Product Class 1: Dialkyl Ethers
37.1.1 Synthesis from Esters, Aldehydes, Ketones, and Acetals by Reduction or Alkylation
L. J. Van Orden, R. Jasti, and S. D. Rychnovsky
37.1.2 Synthesis by Substitution
M. Tsukamoto and M. Kitamura
37.1.3 Synthesis by Addition to Alkenes
D. R. Soenen and C. D. Vanderwal
37.1.4 Synthesis from Other Ethers
F. E. McDonald
37.2 Product Class 2: Epoxides (Oxiranes)
37.2.1 Synthesis from Alkenes by Metal-Mediated Oxidation
H. Adolfsson
37.2.2 Synthesis from Alkenes with Organic Oxidants
D. Goeddel and Y. Shi
37.2.3 Synthesis by Carbonyl Epoxidation
V. K. Aggarwal, M. Crimmin, and S. Riches
37.2.4 Synthesis by Ring Closure
A. K. Yudin and A. Caiazzo
37.3 Product Class 3: Oxetanes and Oxetan-3-ones
A. G. Griesbeck and T. Sokolova
37.4 Product Class 4: Five-Membered and Larger-Ring Oxacycloalk-3-enes
37.4.1 Synthesis by Ring-Closure Reactions, Except Ring-Closing Metathesis
K. Ding and Z. Wang
37.4.2 Synthesis by Ring-Closing Metathesis
S. W. Roberts and J. D. Rainier
37.4.3 Synthesis from Other Cyclic Ethers
K. Iyer and J. D. Rainier
37.5 Product Class 5: Five-Membered and Larger-Ring Oxacycloalkanes
M. Inoue and S. Yamashita
37.6 Product Class 6: Oxonium Salts
C. J. Forsyth and T. J. Murray
37.7 Product Class 7: Oligo- and Monosaccharide Ethers
I. Robina and P. Vogel
37.8 Product Class 8: Ethers as Protecting Groups
S. Petursson
Keyword Index
Author Index
Abbreviations
Introduction
C. J. Forsyth
Introduction
37.1 Product Class 1: Dialkyl Ethers
37.1.1 Synthesis from Esters, Aldehydes, Ketones, and Acetals by Reduction or Alkylation
L. J. Van Orden, R. Jasti, and S. D. Rychnovsky
37.1.1 Synthesis from Esters, Aldehydes, Ketones, and Acetals by Reduction or Alkylation
37.1.1.1 Synthesis of Acyclic Ethers by Reduction of Esters
37.1.1.1.1 Method 1: Hydrosilylation
37.1.1.1.1.1 Variation 1: Under Free-Radical Conditions
37.1.1.1.1.2 Variation 2: With Stoichiometric Lewis Acid
37.1.1.1.1.3 Variation 3: With a Catalytic Manganese Complex
37.1.1.1.2 Method 2: Sodium Borohydride Reduction
37.1.1.1.3 Method 3: Two-Step Reduction Utilizing an α-Acetoxy Ether
37.1.1.1.4 Method 4: Two-Step Reduction Utilizing an S-Alkyl Thioester
37.1.1.2 Synthesis of Acyclic Ethers by Alkylation of Esters
37.1.1.2.1 Method 1: Synthesis by a Two-Step Procedure Utilizing an α-Acetoxy Ether
37.1.1.2.1.1 Variation 1: Organocuprate Addition
37.1.1.2.1.2 Variation 2: Allylstannane Addition
37.1.1.2.1.3 Variation 3: Allylsilane, But-2-enylsilane, and Silyl Ketene Acetal Addition
37.1.1.2.1.4 Variation 4: Trimethylsilyl Cyanide Addition
37.1.1.2.1.5 Variation 5: Organozinc Addition
37.1.1.3 Synthesis of Acyclic Ethers by Reduction of Aldehydes or Ketones
37.1.1.3.1 Method 1: Hydrosilylation
37.1.1.3.1.1 Variation 1: With Iodotrimethylsilane
37.1.1.3.1.2 Variation 2: With Alkoxyhydrosilanes
37.1.1.3.1.3 Variation 3: With Brønsted Acid Catalysis
37.1.1.3.2 Method 2: Hydrogenation
37.1.1.3.3 Method 3: In Situ Formation of Acetals, Followed by Reductive Cleavage
37.1.1.4 Synthesis of Acyclic Ethers by Alkylation of Aldehydes or Ketones
37.1.1.4.1 Method 1: Silyl-Modified Sakurai Reaction
37.1.1.5 Synthesis of Acyclic Ethers by Reduction of Acetals
37.1.1.5.1 Method 1: Metal Hydride Reduction
37.1.1.5.1.1 Variation 1: With Diisobutylaluminum Hydride
37.1.1.5.1.2 Variation 2: With Lithium Aluminum Hydride
37.1.1.5.1.3 Variation 3: With Borane–Dimethyl Sulfide Complex
37.1.1.5.1.4 Variation 4: With Triethylsilane
37.1.1.5.1.5 Variation 5: With Zinc(II) Borohydride
37.1.1.5.2 Method 2: Hydrogenation
37.1.1.6 Synthesis of Acyclic Ethers by Alkylation of Acetals
37.1.1.6.1 Method 1: Addition of Allylsilane Reagents
37.1.1.6.2 Method 2: Addition of Allylstannane Reagents
37.1.1.6.3 Method 3: Other Allylation Methods
37.1.1.6.4 Method 4: Addition of Alka-2,3-dienyl- and Propargylsilanes
37.1.1.6.5 Method 5: Addition of Silyl Enol Ethers and Metal Enolates
37.1.1.6.6 Method 6: Addition of Trimethylsilyl Cyanide
37.1.1.6.7 Method 7: Addition of Grignard Reagents
37.1.1.6.8 Method 8: Addition of Organocuprate Reagents
37.1.1.6.9 Method 9: Addition of Organoaluminum Reagents
37.1.1.6.10 Method 10: Cleavage with Lithium Metal
37.1.1.7 Synthesis of Acyclic Ethers by Alkylation of α-Halo Ethers
37.1.1.7.1 Method 1: Lithiation
37.1.1.7.2 Method 2: Palladium-Mediated Coupling
37.1.1.7.3 Method 3: Addition of Organometallic Reagents
37.1.1.7.4 Method 4: Synthesis by a Two-Step Procedure from an Acetal
37.1.2 Synthesis by Substitution
M. Tsukamoto and M. Kitamura
37.1.2 Synthesis by Substitution
37.1.2.1 Method 1: Oxidation of C—H Bonds
37.1.2.2 Method 2: Intramolecular Oxidative Cyclization of Alcohols
37.1.2.3 Method 3: Ring Opening of Cyclopropanes
37.1.2.4 Method 4: Williamson-Type Reaction of Alkyl Halides
37.1.2.4.1 Variation 1: Using Metal Alkoxides
37.1.2.4.2 Variation 2: With Alcohols in the Presence of Base
37.1.2.4.3 Variation 3: From Halo Alcohols
37.1.2.5 Method 5: Synthesis from Sulfonic and Sulfuric Acid Esters
37.1.2.5.1 Variation 1: Using Dialkyl Sulfates
37.1.2.5.2 Variation 2: Using Trifluoromethanesulfonates
37.1.2.5.3 Variation 3: Using 4-Toluenesulfonates
37.1.2.5.4 Variation 4: Using Methanesulfonates
37.1.2.6 Method 6: Synthesis from Esters of Phosphorus Acids
37.1.2.7 Method 7: Synthesis from Carbonates
37.1.2.8 Method 8: Synthesis from Trichloroacetimidates
37.1.2.9 Method 9: Synthesis from Oxalate Esters
37.1.2.10 Method 10: Synthesis Using Meerwein’s Reagent
37.1.2.11 Method 11: Synthesis from Sulfonium and Selenonium Salts
37.1.2.12 Method 12: Synthesis from Ammonium Salts
37.1.2.13 Method 13: Synthesis from Phosphonium Salts
37.1.2.14 Method 14: Synthesis from Diazo Compounds
37.1.2.14.1 Variation 1: From Diazoalkanes
37.1.2.14.2 Variation 2: From Diazo(trimethylsilyl)methane
37.1.2.14.3 Variation 3: From Diazo Carbonyl Compounds
37.1.2.15 Method 15: Synthesis from Alcohols Using Brønsted Acids
37.1.2.16 Method 16: Synthesis from Alcohols Using Pentavalent Phosphorus Reagents
37.1.2.17 Method 17: Synthesis from Alcohols under Mitsunobu Conditions
37.1.2.18 Method 18: Synthesis from Alcohols Using Carbodiimides
37.1.2.19 Method 19: Synthesis of Ethers from Alcohols by Lewis Acids and Transition-Metal Complexes
37.1.2.20 Method 20: Synthesis from Alcohols Using a Catalytic Amount of Base
37.1.2.21 Method 21: Reaction of Di-tert-butyl Peroxide with Grignard or Organolithium Reagents
37.1.2.22 Method 22: Reaction of tert-Butyl Peroxybenzoates with Grignard Reagents
37.1.3 Synthesis by Addition to Alkenes
D. R. Soenen and C. D. Vanderwal
37.1.3 Synthesis by Addition to Alkenes
37.1.3.1 Method 1: Electrophilic Haloetherification
37.1.3.1.1 Variation 1: Of Isolated Alkenes
37.1.3.1.2 Variation 2: Of Allenes
37.1.3.1.3 Variation 3: Of Conjugated Alkenes
37.1.3.1.4 Variation 4: Of α,β-Unsaturated Carbonyl Compounds
37.1.3.2 Method 2: Electrophilic Alkoxymercuration
37.1.3.3 Method 3: Electrophilic Alkoxyselanylation
37.1.3.3.1 Variation 1: General Reaction
37.1.3.3.2 Variation 2: Selenium-Reagent-Catalyzed Tandem Alkoxyselanylation–Oxidative Deselanylation
37.1.3.3.3 Variation 3: Diastereoselective, Alkene-Controlled Alkoxyselanylation
37.1.3.3.4 Variation 4: Diastereoselective Additions by Selenium Reagent Control
37.1.3.4 Method 4: Base-Catalyzed Conjugate Addition of Alcohols to Electron-Deficient Alkenes
37.1.3.4.1 Variation 1: General Reaction
37.1.3.4.2 Variation 2: Diastereoselective Reaction Controlled by Resident Stereogenicity of the Alkene
37.1.3.4.3 Variation 3: Diastereoselective Reaction Controlled by Resident Stereogenicity of the Alcohol
37.1.3.4.4 Variation 4: Diastereoselective Reaction Achieved by Selective Protonation
37.1.3.5 Method 5: Acid-Catalyzed Addition of Alcohols to Isolated Alkenes
37.1.3.6 Method 6: Uncatalyzed Addition of Alcohols
37.1.3.6.1 Variation 1: To Conjugated Alkenes
37.1.3.6.2 Variation 2: Diastereoselective Methods: Alkene Controlled
37.1.3.7 Method 7: Palladium-Catalyzed Addition to Alkenes
37.1.3.8 Method 8: Transition-Metal-Catalyzed Allylic Etherification
37.1.3.9 Method 9: Photochemical Alkoxylation
37.1.3.9.1 Variation 1: Of Isolated Alkenes
37.1.3.9.2 Variation 2: Of Conjugated Alkenes
37.1.3.9.3 Variation 3: Of α,β-Unsaturated Carbonyl Compounds
37.1.3.9.4 Variation 4: Stereoselective Photoalkoxylation of Alkenes
37.1.3.10 Method 10: Radical Alkoxylation of Alkenes
37.1.3.11 Method 11: Electrochemical Alkoxylation of Alkenes
37.1.4 Synthesis from Other Ethers
F. E. McDonald
37.1.4 Synthesis from Other Ethers
37.1.4.1 Method 1: Transetherification
37.1.4.1.1 Variation 1: Substitution of Benzylic Ethers
37.1.4.1.2 Variation 2: Substitution of Allylic Ethers
37.1.4.1.3 Variation 3: Substitution of Pent-4-enyl Ethers
37.1.4.2 Method 2: Substitution of an α-Hydrogen with Carbon
37.1.4.2.1 Variation 1: From Benzylic Ethers
37.1.4.2.2 Variation 2: From Allylic Ethers
37.1.4.2.3 Variation 3: From Propargylic Ethers
37.1.4.2.4 Variation 4: From Alkyl Ethers
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