Greene's Protective Groups in Organic Synthesis / Edition 4

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Overview

An indispensable reference for any practicing synthetic organic or medicinal chemist, this book continues the tradition of Greene’s as comprehensive in the overall scope of coverage, providing the most relevant and useful examples to illustrate each methodology.
• Presents valuable material, on the application of protective groups in organic chemistry, that is not easily found by casual searching
• Helps chemists to plan, investigate, and carry out organic syntheses in an efficient manner
• Adds over 2800 new references to update since the publication of the last edition
• Reviews of the prior edition: "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)

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Editorial Reviews

From the Publisher
"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)

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Product Details

  • ISBN-13: 9780471697541
  • Publisher: Wiley
  • Publication date: 11/3/2006
  • Edition description: Revised Edition
  • Edition number: 4
  • Pages: 1110
  • Product dimensions: 6.48 (w) x 9.21 (h) x 2.23 (d)

Meet the Author

PETER G. M. WUTS, PHD, is a Senior Research Fellow at Pfizer in Ann Arbor, Michigan.

The late THEODORA W. GREENE, PHD, was the librarian for the Rowland Institute for Science and former assistant editor for Organic Syntheses.

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Table of Contents

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.

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