Protective Groups in Organic Synthesis, 3rd Edition

by Theodora W. Greene (The Rowland Institute for Science); Peter G. M. Wuts (Pharmacia and Upjohn Company)

• ISBN13: 9780471160199
• ISBN10: 0471160199
• Edition: 3rd
• Format: Hardcover
• Copyright: 1999-04-01
• Publisher: Wiley-Interscience

Summary

From the reviews of the previous editions:* "For completeness, the authors . . . include protective groups and techniques for formation and cleavage that are seldom used as well as those that are more common. . . . Anyone who does organic synthesis must have convenient access to this book." -Journal of the American Chemical Society.* "Essential to the modern synthetic organic chemist . . . should be in the libraries of all academic, governmental, and industrial organizations concerned with organic synthesis." -Polymer News.Reflecting the latest advances in protective group methodology, this Third Edition of the proven laboratory reference is expanded by more than 50%, providing readers with a comprehensive compendium of 1,050 of the most useful protective groups as well as 5,350 references to original publications. Protective groups are organized by six major organic functional groups: hydroxyl, amino, carboxyl, carbonyl, sulfhydryl, and phosphate groups (the last new to this edition). Also added in this edition are protection of the alkyne-CH, expanded coverage of protection of all groups, and many new enzymatic methods of protection and deprotection. Each chapter briefly describes the classes of available protective groups, followed by an in-depth look at the chemistry of individual protective groups, their properties, and the best methods of formation and cleavage. Ten reactivity charts with more than 28,000 entries summarize the relative reactivities of 270 commonly used protective groups with 108 reagents. This book will be an indispensable reference for synthetic chemists and students.

Author Biography

THEODORA W. GREENE, PhD, is Assistant Editor for Organic Syntheses and the former librarian for the Rowland Institute for Science. She holds a PhD in Chemistry from Harvard University.<br> <br> G. M. WUTS, PhD, is Senior Scientist at Pharmacia & Upjohn in Kalamazoo, Michigan and has a PhD in Chemistry from Northwestern University.

Table of Contents

Abbreviations	xiii
The Role of Protective Groups in Organic Synthesis	1	(16)
Protection for the Hydroxyl Group, Including 1,2- and 1, 3-Diols	17	(229)
Ethers	23	(126)
Esters	149	(52)
Protection for 1,2- and 1,3-Diols	201	(45)
Protection for Phenols and Catechols	246	(47)
Protection for Phenols	249	(38)
Ethers	249	(27)
Esters	276	(11)
Protection for Catechols	287	(6)
Cyclic Acetals and Ketals	287	(3)
Cyclic Esters	290	(3)
Protection for the Carbonyl Group	293	(76)
Acetals and Ketals	297	(51)
Miscellaneous Derivatives	348	(16)
Monoprotection of Dicarbonyl Compounds	364	(5)
Protection for the Carboxyl Group	369	(85)
Esters	373	(69)
Amides and Hydrazides	442	(12)
Protection for the Thiol Group	454	(40)
Thioethers	457	(25)
Thioesters	482	(5)
Miscellaneous Derivatives	487	(7)
Protection for the Amino Group	494	(160)
Carbamates	503	(47)
Amides	550	(23)
Special--NH Protective Groups	573	(42)
Protection for Imidazoles, Pyrroles, and Indoles	615	(17)
Protection for Amides	632	(22)
Protection for the Alkyne--CH	654	(6)
Protection for the Phosphate Group	660	(41)
Reactivities, Reagents, and Reactivity Charts	701	(48)
Reactivities	701	(1)
Reagents	702	(3)
Reactivity Charts	705	(44)
Protection for the Hydroxyl Group: Ethers	708	(4)
Protection for the Hydroxyl Group: Esters	712	(4)
Protection for 1,2- and 1,3-Diols	716	(4)
Protection for Phenols and Catechols	720	(4)
Protection for the Carbonyl Group	724	(4)
Protection for the Carboxyl Group	728	(4)
Protection for the Thiol Group	732	(4)
Protection for the Amino Group: Carbamates	736	(4)
Protection for the Amino Group: Amides	740	(4)
Protection for the Amino Group: Special--NH Protective Groups	744	(5)
Index	749