Protective Groups in Organic Synthesis has long 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.

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

Contents

The Role of Protective Groups in Organic Synthesis

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

• Ethers
• Esters
• Protection for 1,2- and 1,3-Diols

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

Protection for the Carbonyl Group

• Acetals and Ketals
• Miscellaneous Derivatives
• Monoprotection of Dicarbonyl Compounds

Protection for the Carboxyl Group

• Esters
• Amides and Hydrazides
• Protection of Boronic Acids
• Protection of Sulfonic Acids

Protection for the Thiol Group

• Thioethers
• Thioesters
• Miscellaneous Derivatives

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

Protection for the Alkyne —CH

Protection for the Phosphate Group

• Some General Methods for Phosphate Ester Formation
• Removal of Protective Groups from Phosphorus
• Alkyl Phosphates
• Phosphates Cleaved by Cyclodeesterification
• Benzyl Phosphates
• Phenyl Phosphates
• Photochemically Cleaved Phosphate Protective Groups
• Amidates
• Miscellaneous Derivatives

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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