Preface to the Fourth Edition .................................. ix
Preface to the Third Edition ................................... xi
Preface to the Second Edition ................................ xiii
Preface to the First Edition ................................... xv
Abbreviations ................................................ xvii
1 The Role of Protective Groups in Organic Synthesis ........... 1
2 Protection for the Hydroxyl Group, Including 1,2- and
1,3-Diols ................................................... 16
Ethers, 24 Esters .......................................... 222
Protection for 1,2- and 1,3-Diols .......................... 299
3 Protection for Phenols and Catechols ....................... 367
Protection for Phenols ..................................... 370
Ethers ..................................................... 370
Silyl Ethers ............................................... 406
Esters ..................................................... 410
Carbonates ................................................. 416
Aryl Carbamates ............................................ 419
Phosphinates ............................................... 420
Sulfonates ................................................. 421
Protection for Catechols ................................... 424
Cyclic Acetals and Ketals .................................. 424
Cyclic Esters .............................................. 428
Protection for 2-Hydroxybenzenethiols ...................... 430
4 Protection for the Carbonyl Group .......................... 431
Acetals and Ketals ......................................... 435
Miscellaneous Derivatives .................................. 506
Monoprotection of Dicarbonyl Compounds ..................... 528
5 Protection for the Carboxyl Group .......................... 533
Esters ..................................................... 538
Amides and Hydrazides ...................................... 632
Protection of Boronic Acids ................................ 643
Protection of Sulfonic Acids ............................... 645
6 Protection for the Thiol Group ............................. 647
Thioethers ................................................. 650
Thioesters ................................................. 682
Miscellaneous Derivatives .................................. 687
7 Protection for the Amino Group ............................. 696
Carbamates ................................................. 706
Amides ..................................................... 773
Special-NH Protective Groups ............................... 803
Protection for Imidazoles, Pyrroles, Indoles, and other
Aromatic Heterocycles ...................................... 872
Protection for the Amide -NH ............................... 894
Protection for the Sulfonamide -NH ......................... 916
8 Protection for the Alkyne -CH .............................. 927
9 Protection for the Phosphate Group ......................... 934
Some General Methods for Phosphate Ester Formation ......... 939
Removal of Protective Groups from Phosphorus ............... 940
Alkyl Phosphates ........................................... 944
Phosphates Cleaved by Cyclodeesterification ................ 952
Benzyl Phosphates .......................................... 966
Phenyl Phosphates .......................................... 972
Photochemically Cleaved Phosphate Protective Groups ........ 980
Amidates ................................................... 983
Miscellaneous Derivatives .................................. 985
10 Reactivities, Reagents, and Reactivity Charts .............. 986
Reactivities ............................................... 986
Reagents ................................................... 987
Reactivity Charts .......................................... 990
1 Protection for the Hydroxyl Group: Ethers ............... 992
2 Protection for the Hydroxyl Group: Esters ............... 997
3 Protection for 1,2-and 1,3-Diols ....................... 1001
4 Protection for Phenols and Catechols ................... 1005
5 Protection for the Carbonyl Group ...................... 1009
6 Protection for the Carboxyl Group ...................... 1013
7 Protection for the Thiol Group ......................... 1017
8 Protection for the Amino Group: Carbamates ............. 1021
9 Protection for the Amino Group: Amides ................. 1025
10 Protection for the Amino Group: Special -NH
Protective Groups ...................................... 1029
11 Selective Deprotection of Silyl Ethers ................. 1033
Index ........................................................ 1053
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