Protecting Groups in Organic Synthesis Postgraduate Chemistry Series

by Hanson, James R.

• ISBN13: 9781850759577
• ISBN10: 185075957X
• Edition: 1st
• Format: Hardcover
• Copyright: 1999-11-15
• Publisher: Wiley-Blackwell

Summary

This volume provides, at postgraduate student level, an accessible introduction to a topic of central importance in organic synthesis. It covers the main functional groups requiring protection in organic synthesis, explaining why a particular protecting agent works and how an agent should be chosen. Emphasis is placed on what a protecting group is doing chemically to the structure that it is protecting. Attention is given to removal of the protecting group.This is a clear and thoughtful book, which concentrates on explaining the chemistry. It also provides a convenient point of entry to the primary literature.

Author Biography

James R. Hansen is a professor of history at Auburn University in Alabama. His book From the Ground Up won the History Book Award of the American Institute of Aeronautics and Astronautics in 1988.

Table of Contents

Introduction	1	(8)
The Protection of alcohols	8	(29)
Introduction	8	(1)
The protection of aliphatic alcohols as ethers	8	(16)
Methyl enters	8	(2)
Allyl and benzyl ethers	10	(1)
Triphenylmethyl ethers	11	(1)
Substituted benzyl ether protecting groups	12	(3)
Oxygen-substituted ethers	15	(6)
Silyl ethers	21	(3)
Esters as protecting groups of alcohols	24	(6)
Acetate esters	25	(1)
Modified esters	26	(4)
The protection of 1,2-diols and 1,3-diols	30	(5)
The protection of phenols	35	(2)
The protection of aldehydes and ketones	37	(16)
Introduction	37	(1)
Acetals and protecting groups	37	(1)
1,3-Dioxolanes and related protecting groups	38	(5)
Thioacetals as protecting groups	43	(3)
Enol ethers and enamines as protecting groups	46	(3)
Nitrogen derivatives as protecting groups	49	(2)
The protection of 1,2-and 1,3-diketones	51	(2)
The protection of carboxylic acids	53	(17)
Introduction	53	(1)
Methods of esterification	53	(2)
Activation of the esterifying alcohol	55	(2)
Activation of the carboxylic acid	57	(4)
The hydrolysis of esters	61	(7)
Orthoesters as protecting groups	68	(2)
The protection of the amino group	70	(18)
Introduction	70	(1)
Alkyl and related protecting groups	70	(2)
Imines and enamines as protecting groups	72	(2)
Amides as protecting groups for amines	74	(6)
The protection of amino groups in amino acids	80	(7)
Protection of side chain amino groups in amino acids	87	(1)
The protection of thiols	88	(4)
Introduction	88	(1)
Thioethers	88	(1)
The protection of thiols as acetal derivatives	89	(2)
Thioesters as protecting groups	91	(1)
The protection of unsaturated systems	92	(10)
The protection of alkenes	92	(2)
The protection of dienes	94	(2)
The protection of alkynes	96	(2)
Positional protective groups in aromatic substitution	98	(4)
Some experimental methods	102	(15)
The protection of alcohols	103	(6)
The preparation of a methyl ether	103	(1)
The Preparation of a tetrahydrophyranyl ether	103	(1)
The Preparation of a methoxymethyl ether	104	(1)
The preparation of a triphenylmethyl ether	105	(1)
Methylation of a phenol by using dimethyl sulfate	105	(1)
Methylation of a phenol by using methyl toluene-p-sulfonate	106	(1)
The preparation of a t-butyldimethylsilyl ether	106	(1)
Hydrolysis of a t-butyldimethylsilyl ether	106	(1)
The preparation of an acetate ester	107	(1)
Hydrolysis of an acetate ester	108	(1)
The preparation of an isopropylidene derivative	108	(1)
The protection of aldehydes and ketones	109	(3)
The preparation of a 1,3-dioxolane derivative	109	(1)
The preparation of an oxime	110	(1)
The preparation of an enol ether of a β-diketone	110	(1)
The preparation of pyrrolidine enamine	111	(1)
The preparation of hydroxymethylene ether	111	(1)
The protection of carboxylic acids	112	(2)
Methylation with diazomethane	113	(1)
Methylation with dimethylformamide dimethylacetal	113	(1)
Methylation with caesium fluoride and methyl iodide	114	(1)
The protection of the amino group	114	(3)
The preparation of acetanilide	114	(1)
Acetylation of anthranilic acid	115	(1)
The protection of p-bromoaniline as a dimethylpyrrole	115	(1)
The preparation of a carbobenzyloxy derivative	115	(1)
The preparation of a t-butoxycarbonyl derivative	116	(1)
The preparation of an N-phthalyl derivative	116	(1)
Appendix	117	(3)
References	120	(7)
Index	127