Protecting Groups, 3rd edition

General description

Provides a concise and understandable presentation of modern protecting group methods. This edition is a valuable addition to the synthetic chemist′s bookshelf. The introductory chapter provides a sophisticated overview of the application of protecting groups in contemporary syntheses.

At the heart of the book are seven chapters which deal authoritatively and thoroughly with the protection of the various core functional groups, from carbonyl to amino. The final chapter presents an insight into the realities of synthetic practice and twenty-five problems for people who love to understand chemistry.

Table of Contents

1. Protecting Groups: an Overview
1.1 Death, Taxes, and Protecting Groups
1.2 Deprotection: The Concept of Orthogonal Sets
1.3 Relay Deprotection
1.4 Transprotection
1.5 Mutual Protection
1.6 Temporary Protection
1.7 Protecting Groups as Not-So-Innocent Bystanders
1.8 Protecting Groups and Solid Phase Synthesis
1.9 Reviews
2. Carbonyl Protecting Groups
2.1 Introduction
2.2 O,O-Acetals
2.3 S,S-Acetals
2.4 O,S-Acetals
2.5 N,O-Acetals
2.6 Cynaohydrins
2.7 Orthoester Derivatives
2.8 Oxazolines
2.9 Reviews
3. Diol Protecting Groups
3.1 Introduction
3.2 O,O-Acetals
3.3 1,2-Diacetals
3.4 Silylene Derivatives
3.5 1,1,3,3-Tetraisopropyldisiloxanylidene Derviratives
3.6 N,O- Acetals for the Protection of 1,2 and 1,3-Amino Alcohols
3.7 Reviews
4. Hydroxyl Protecting Groups
4.1 Introduction
4.2 Silyl Ethers
4.3 Alkyl Ethers
4.4 Alkoxymethyl Ethers
4.5 Tetrahydropyranyl (THP) and Related Ethers
4.6 Methylthiomethyl (MTM) Ethers
4.7 Esters
4.8 Carbonates
4.9 Reviews
5. Thiol Protecting Groups
5.1 Introduction
5.2 Thioether Derivatives
5.3 Thiocarbonate Derivatives
5.4 Disulfides as Protecting Groups and Targets
5.5 Reviews
6. Carboxyl Protecting Groups
6.1 Introduction
6.2 General Commnets on the Esterification of Carboxylic Acids
6.3 Methyl Esters and Derivatives
6.4 Alkoxyalkyl Esters
6.5 Esters Cleaved by b-Elimination Reactions
6.6 Silyl Esters
6.7 Reviews
7. Phosphate Protecting Groups
7.1 Introduction
7.2 The Reaction of Phosphate Esters with Nucleophiles
7.3 Alkyl Esters
7.4 Esters Cleaved by b-Elimination Reactions
7.5 Review
8. Amino Protecting Groups
8.1 Introduction
8.2 Imides and Amides
8.3 Carbamates
8.4 Sulfonyl Derviatives
8.5 N-Sulfenyl Derivatives
8.6 N-Alkyl Derivatives
8.7 N-Silyl Derivatives
8.8 Imines and Enamine
8.9 Special Cases
8.10 Reviews