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Greene's Protective Groups in Organic Synthesis, 4th Edition

Greene's Protective Groups in Organic Synthesis, 4th Edition

Peter G. M. Wuts, Theodora W. Greene

ISBN: 978-0-471-69754-1

Oct 2006

1110 pages

Description

The Most Comprehensive Guide to Protective Groups in Organic Synthesis Currently Available

For more than twenty-five years, Protective Groups in Organic Synthesis has been the definitive guide for organic chemists in designing synthetic routes. Now in its fourth edition, the text continues to be a uniquely comprehensive and an indispensable reference for both synthetic organic and medicinal chemists who want to control the reactivity of the most common functional groups during a synthetic sequence.

The Fourth Edition includes significant developments in protective group chemistry since 1998. In addition to incorporating new protective groups now available to the synthetic organic chemist, such as the uniquely removable 2-methoxybenzenesulfonyl group for the protection of amines, the book also covers new techniques for the formation and cleavage of existing protective groups, providing the most relevant and useful examples to illustrate each methodology. The content is organized around the functional group to be protected (ethers, acids, carbonyl groups, amines, amides, phenols, etc.), and ranges from the simplest to the most complex highly specialized protective groups.

New features of the Fourth Edition include:

  • The addition of numerous new protective groups, such as the fluorous family
  • New methods for the cleavage and introduction of many of the classic protective groups highlighting selectivity issues when reported in the literature
  • Expanded coverage of the unexpected side reactions that occur with protective groups
  • A new chart covering the selective deprotection of silyl ethers
  • 3,100 new references from the professional literature, complete through the end of 2005
Preface to the Fourth Edition.

Preface to the Third Edition.

Preface to the Second Edition.

Preface to the First Edition.

Abbreviations.

1. The Role of Protective Groups in Organic Synthesis.

2. Protection for the Hydroxyl Group, Including 1,2- and 1,3-Diols.

Ethers.

Esters.

Protection for 1,2- and 1,3-Diols.

3. Protection for Phenols and Catechols.

Protection for Phenols.

Ethers.

Silyl Ethers.

Esters.

Carbonates.

Aryl Carbamates.

Phosphinates.

Sulfonates.

Protection for Catechols.

Cyclic Acetals and Ketals.

Cyclic Esters.

Protection for 2-Hydroxybenzenethiols.

4. Protection for the Carbonyl Group.

Acetals and Ketals.

Miscellaneous Derivatives.

Monoprotection of Dicarbonyl Compounds.

5. Protection for the Carboxyl Group.

Esters.

Amides and Hydrazides.

Protection of Boronic Acids.

Protection of Sulfonic Acids.

6. Protection for the Thiol Group.

Thioethers.

Thioesters.

Miscellaneous Derivatives.

7. Protection for the Amino Group.

Carbamates.

Amides.

Special —NH Protective Groups.

Protection for Imidazoles, Pyrroles, Indoles, and other Aromatic Heterocycles.

Protection for the Amide —NH.

Protection for the Sulfonamide —NH.

8. Protection for the Alkyne —CH.

9. Protection for the Phosphate Group.

Some General Methods for Phosphate Ester Formation.

Removal of Protective Groups from Phosphorus.

Alkyl Phosphates.

Phosphates Cleaved by Cyclodeesterifi cation.

Benzyl Phosphates.

Phenyl Phosphates.

Photochemically Cleaved Phosphate Protective Groups.

Amidates.

Miscellaneous Derivatives.

10. Reactivities, Reagents, and Reactivity Charts.

Reactivities.

Reagents.

Reactivity Charts.

1 Protection for the Hydroxyl Group: Ethers.

2 Protection for the Hydroxyl Group: Esters.

3 Protection for 1,2- and 1,3-Diols.

4 Protection for Phenols and Catechols.

5 Protection for the Carbonyl Group.

6 Protection for the Carboxyl Group.

7 Protection for the Thiol Group.

8 Protection for the Amino Group: Carbamates.

9 Protection for the Amino Group: Amides.

10 Protection for the Amino Group: Special —NH Protective Groups.

11 Selective Deprotection of Silyl Ethers.

Index.

"An essential bible for the library or personal bookshelf of chemists performing complex synthesis." (CHOICE, May 2007)

"...the most up-to-date compilation available...should be an integral part of all institutional libraries...it is also highly recommended that individuals...maintain their own copy..." (Journal of Medicinal Chemistry, March 8, 2007)

"...continues to be a comprehensive guide to the techniques for the formation and cleavage of protective groups." (Journal of the American Chemical Society, January 31, 2007)