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Esterification: Methods, Reactions, and Applications

Esterification: Methods, Reactions, and Applications

Junzo Otera

ISBN: 978-3-527-60607-8

Aug 2006

313 pages

Select type: E-Book



Here, Professor J. Otera brings together for the first time the combined knowledge about this elementary yet multifaceted reaction. Starting from the methodical basics right up to practical applications, this book represents a comprehensive overview of this type of reaction, saving readers time-consuming research among the literature - and not just in practical matters. All set to become a standard reference for every organic chemist.

From the contents:
Reaction of Alcohols with Carboxylic Acids and Their Derivatives
Reactions with Carboxylic Acids
Reaction with Esters: Transesterification
Reaction with Acid Anhydrides
Reaction with Acid Halides and Related Compounds
Conversion of Alcohols to Esters through Carbonylation
Kinetic Resolution
Enzymatic Resolution
Nonenzymatic Resolution
Asymmetric Desymmetrization
Deacetylation through Transesterification
Selective Esterification
Applications to Natural Product Synthesis
New Reaction Media
Industrial Uses



Part I: Methodology.

1 Reaction of Alcohols with Carboxylic Acids and their Derivatives.

1.1 Reaction with Carboxylic Acids.

1.1.1 Without Activator.

1.1.2 Acid Catalysts.

1.1.3 Base Activators.

1.1.4 Carbodiimide Activators.

1.1.5 The Mitsunobu Reaction.

1.1.6 Activation of Carboxylic Acids.

1.1.7 Enzymes.

1.1.8 p-Acids.

1.2 Reaction with Esters: Transesterification.

1.2.1 Without Activator.

1.2.2 Acid Catalysts.

1.2.3 Base Activators.

1.2.4 Other Activators.

1.2.5 Enzymes.

1.3 Reaction with Acid Anhydrides.

1.3.1 Without Activator.

1.3.2 Acid Catalysts.

1.3.3 Base Activators.

1.3.4 Enzymes.

1.3.5 Mixed Anhydrides.

1.4 Reaction with Acid Halides and Other Acyl Derivatives.

1.4.1 Without Activator.

1.4.2 Acid Catalysts.

1.4.3 Base Activators.

1.4.4 Other Activators.

1.4.5 Enzymes.

2 Use of Tin and Other Metal Alkoxides.

3 Conversion of Carboxylic Acids into Esters without Use of Alcohols.

3.1 Treatment with Diazomethane.

3.2 Reaction with Alkyl Halides.

3.3 Treatment with Other Electrophiles.

4 Ester-Interchange Reactions.

Part II Synthetic Applications.

5 Kinetic Resolution.

5.1 Enzymatic Resolution.

5.2 Nonenzymatic Resolution.

5.3 Dynamic Kinetic Resolution.

5.4 Parallel Kinetic Resolution.

6 Asymmetric Desymmetrization.

7 Miscellaneous Topics.

7.1 Selective Esterification.

7.1.1 Differentiation between Primary, Secondary, and Tertiary Alcohols and Phenols.

7.1.2 Differentiation between Identical or Similar Functions.

7.2 Use of Theoretical Amounts of Reactants.

7.3 New Reaction Media.

7.4 Application to Natural Products Synthesis.

8 Industrial Uses.

8.1 Polyesters.

8.2 Oils and Fats.

8.2.1 Food Emulsifiers.

8.2.2 Soaps.

8.3 Amino Acid Esters.

8.4 Flavoring Agents and Fragrances.

8.5 Pyrethroids.


Reference Code Index.



"...Otera's book does a good job, concisely covering the esterification methodology literature from 1990 to 1999, and that survey will be useful to synthetic organic chemists..." (Angewandte Chemie International Edition, Vol. 43)