Peter G. M. Wuts

Greene's Protective Groups in Organic Synthesis (eBook, ePUB)

• Format: ePub

Produktbeschreibung

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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Produktdetails

• Verlag: John Wiley & Sons
• Seitenzahl: 1408
• Erscheinungstermin: 8. August 2014
• Englisch
• ISBN-13: 9781118905128
• Artikelnr.: 41355829

Autorenporträt

Peter G.M. Wuts is a Distinguished Scientist at Kalexsyn, Inc. in Kalamazoo, Michigan.

Inhaltsangabe

Preface to the Fifth Edition xi
Preface to the Fourth Edition xiii
Preface to the Third Edition xv
Preface to the Second Edition xvii
Preface to the First Edition xix
Abbreviations xxi
1. The Role of Protective Groups in Organic Synthesis 1
Properties of a Protective Group 1
Historical Development 2
Development of New Protective Groups 2
Selection of a Protective Group from This Book 4
Synthesis of Complex Substances: Two Examples (As used in the Synthesis of
Himastatin and Palytoxin) of the Selection Introduction and Removal of
Protective Groups 5
Synthesis of Himastatin 5
Synthesis of Palytoxin Carboxylic Acid 9
2. Protection for the Hydroxyl Group Including 12- and 13-Diols 17
Ethers 26
Substituted Methyl Ethers 33
Substituted Ethyl Ethers 87
Methoxy-Substituted Benzyl Ethers 146
Silyl Ethers 201
Esters 271
Bisfluorous Chain-Type Propanoate (Bfp-OR) Ester 307
Proximity-Assisted Deprotection for Ester Cleavage 329
Miscellaneous Esters 336
Sulfonates Sulfenates and Sulfinates as Protective Groups for Alcohols 337
Carbonates 347
Carbamates 371
Protection for 12- and 13-Diols 375
Monoprotection of Diols 375
Cyclic Acetals and Ketals 385
Chiral Ketones 446
Cyclic Orthoesters 447
Silyl Derivatives 456
Cyclic Carbonates 465
Cyclic Boronates 468
3. Protection for Phenols and Catechols 472
Protection for Phenols 475
Ethers 475
Silyl Ethers 522
Esters 528
Carbonates 535
Carbamates 538
Phosphinates 540
Sulfonates 541
Protection for Catechols (12-Dihydroxybenzenes) 545
Cyclic Acetals and Ketals 545
Cyclic Esters 551
Protection for 2-Hydroxybenzenethiols 552
4. Protection for the Carbonyl Group 554
Acetals and Ketals 559
Acyclic Acetals and Ketals 559
Cyclic Acetals and Ketals 576
Chiral Acetals and Ketals 611
Dithio Acetals and Ketals 615
Cyclic Dithio Acetals and Ketals 620
Monothio Acetals and Ketals 644
Diseleno Acetals and Ketals 649
Miscellaneous Derivatives 650
O-Substituted Cyanohydrins 650
Substituted Hydrazones 654
Oxime Derivatives 661
12-Adducts to Aldehydes and Ketones 669
Cyclic Derivatives 674
Protection of the Carbonyl Group as Enolate Anions Enol Ethers Enamines and
Imines 676
Monoprotection of Dicarbonyl Compounds 679
Selective Protection of ¿- and ß-Diketones 679
Cyclic Ketals Monothio and Dithio Ketals 684
5. Protection for the Carboxyl Group 686
Esters 692
General Preparation of Esters 692
General Cleavage of Esters 699
Transesterification 704
Enzymatically Cleavable Esters 711
Substituted Methyl Esters 723
2-Substituted Ethyl Esters 739
26-Dialkylphenyl Esters 768
Substituted Benzyl Esters 775
Silyl Esters 792
Activated Esters 796
Miscellaneous Derivatives 799
Stannyl Esters 812
Amides and Hydrazides 812
Amides 820
Hydrazides 825
Protection of Sulfonic Acids 828
Protection of Boronic Acids 831
6. Protection for the Thiol Group 837
Thioethers 841
S-Diphenylmethyl Substituted S-Diphenylmethyl and S-Triphenylmethyl
Thioethers 855
Substituted S-Methyl Derivatives: Monothio Dithio and Aminothio Acetals 864
Substituted S-Ethyl Derivatives 875
Silyl Thioethers 880
Thioesters 881
Thiocarbonate Derivatives 883
Thiocarbamate Derivatives 885
Miscellaneous Derivatives 886
Unsymmetrical Disulfides 886
Sulfenyl Derivatives 888
Protection for Dithiols: Dithio Acetals and Ketals 891
Protection for Sulfides 892
S-P Derivatives 893
Protection for the Amino Thiol Group 894
7. Protection for the Amino Group 895
Carbamates 907
Substituted Ethyl Carbamates 921
Carbamates Cleaved by a 16-Elimination 977
Carbamates Cleaved by ß-Elimination 979
Photolytically Cleaved Carbamates 983
Miscellaneous Carbamates 987
Urea-Type Derivatives 989
Amides 990
Assisted Cleavage of Amides 1007
Bisprotection of Amines 1009
Special -Nh Protective Groups 1025
N-Alkyl and N-Aryl Amines 1025
Imine Derivatives 1060
Enamine Derivatives 1069
Quaternary Ammonium Salts 1072
N-Heteroatom Derivatives 1073
N-Metal Derivatives 1073
N-N Derivatives 1078
N-P Derivatives 1083
N-Si Derivatives 1086
N-S Derivatives 1088
Protection of Amino Alcohols 1116
Protection for Imidazoles Pyrroles Indoles and Other Aromatic
Heterocycles 1120
N-Sulfonyl Derivatives 1120
Carbamates 1124
N-Alkyl and N-Aryl Derivatives 1129
N-Trialkylsilylamines R2N-SiR03 1131
N-Allylamine CH2.CHCH2NR2 1131
N-Benzylamine (Bn-NR2) PhCH2-NR2 1132
Amino Acetal Derivatives 1137
Amides 1141
Protection for the Amide -NH 1151
Protection for the Sulfonamide -NH 1182
8. Protection for the Alkyne -CH 1194
9. Protection for the Phosphate Group 1203
Some General Methods for Phosphate Ester Formation 1209
Removal of Protective Groups from Phosphorus 1210
Alkyl Phosphates 1214
Phosphates Cleaved by Cyclodeesterification 1223
2-Substituted Ethyl Phosphates 1228
Haloethyl Phosphates 1236
Benzyl Phosphates 1239
Phenyl Phosphates 1246
Photochemically Cleaved Phosphate Protective Groups 1254
Amidates 1258
Miscellaneous Derivatives 1261
10. Reactivities Reagents and Reactivity Charts 1263
Reactivities 1263
Reagents 1264
Reactivity Charts 1267
Reactivity Chart 1. Protection for Hydroxyl Group: Ethers 1269
Reactivity Chart 2. Protection for Hydroxyl Group: Esters 1274
Reactivity Chart 3. Protection for 12- and 13-Diols 1278
Reactivity Chart 4. Protection for Phenols and Catechols 1282
Reactivity Chart 5. Protection for the Carbonyl Group 1286
Reactivity Chart 6. Protection for the Carboxyl Group 1290
Reactivity Chart 7. Protection for the Thiol Group 1294
Reactivity Chart 8. Protection for the Amino Group: Carbamates 1298
Reactivity Chart 9. Protection for the Amino Group: Amides 1302
Reactivity Chart 10. Protection for the Amino Group: Special -NH Protective
Groups 1306
Reactivity Chart 11. Selective Deprotection of Silyl Ethers 1311
Index 1333