Protecting Groups in Organic Synthesis

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.

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.

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

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Protecting Groups in Organic Synthesis Postgraduate Chemistry Series

Summary

Author Biography

Table of Contents

Supplemental Materials