Aziridines and Epoxides in Organic Synthesis

1. Auflage 2006
ISBN: 978-3-527-31213-9
Verlag: WILEY-VCH

Buch, Englisch, 494 Seiten, Format (B × H): 178 mm x 246 mm, Gewicht: 1093 g

Aziridines and epoxides are among the most widely used intermediates in organic synthesis, acting as precursors to complex molecules due to the strains incorporated in their skeletons. Besides their importance as reactive intermediates, many biologically active compounds also contain these three-membered rings.
Filling a gap in the literature, this clearly structured book presents the much needed information in a compact and concise way. The renowned editor has succeeded in gathering together excellent authors to cover synthesis, applications, and the biological aspects in equal depth.
Divided roughly equally between aziridines and epoxides, the twelve chapters discuss:

* Synthesis of aziridines
* Nucleophilic ring-opening of aziridines and epoxides
* Organic synthesis with aziridine building blocks
* Vinyl aziridines in organic synthesis
* Diastereoselective aziridination reagents
* Synthetic aspects of aziridinomitocene chemistry
* Biosynthesis of biologically important aziridines
* Organic catalysis of epoxide and aziridine ring formation
* Metal-mediated synthesis of epoxides
* Asymmetric epoxide ring opening chemistry
* Epoxides in complex molecule synthesis
* Biological activity of epoxide-containing molecules
A high-quality reference manual for academic and industrial chemists alike.

Zielgruppe

Organiker, Katalyse-Chemiker, Chemische Industrie, Bibliotheken

Autoren/Hrsg.

Yudin, Andrei K.

Fachgebiete

• Naturwissenschaften Chemie Organische Chemie Organometallchemie
• Naturwissenschaften Chemie Organische Chemie Supramolekularchemie
• Naturwissenschaften Chemie Anorganische Chemie Nichtmetallische Chemie

Inhaltsverzeichnis

ASYMMETRIC SYNTHESIS OF EPOXIDES AND AZIRIDINES FROM ALDEHYDES AND IMINES

Asymmetric Epoxidation of Carbonyl Compounds

Asymmetric Aziridination of Imines

VINYLAZIRIDINES IN ORGANIC SYNTHESIS

Direct Synthesis of Vinylaziridines

Ring-opening Reactions with Nucleophiles

Isomerization Including Rearrangement

Cycloaddition

Electron Transfer to Vinylaziridines

ASYMMETRIC SYNTHESES WITH AZIRIDINECARBOXYLATE AND AZIRIDINEPHOSPHONATE BUILDING BLOCKS

Preparation of Aziridine-2-carboxylates and Aziridine-2-phosphonates

Reactions of Aziridine-2-carboxylates and Aziridine-2-phosphonates

Applications in Natural Product Syntheses

SYNTHESIS OF AZIRIDINES

Overview and General Features

METALATED EPOXIDES AND AZIRIDINES IN SYNTHESIS

Metalated Epoxides

Metalated Aziridines

METAL-CATALYZED SYNTHESIS OF EPOXIDES

Oxidants Available for Selective Transition Metal-catalyzed Epoxidation

Epoxidations of Olefins Catalyzed by Early Transition Metals

Chromium-, Molybdenum-, and Tungsten-catalyzed Epoxidations

Manganese-catalyzed Epoxidations

Rhenium-catalyzed Epoxidations

Iron-catalyzed Epoxidations

Ruthenium-catalyzed Epoxidations

CATALYTIC ASYMMETRIC EPOXIDE RING-OPENING CHEMISTRY

Enantioselective Nucleophilic Addition to Meso-Epoxides

Kinetic Resolution of Racemic Epoxides

Enantioselective Rearrangements of Epoxides

EPOXIDES IN COMPLEX MOLECULE SYNTHESIS

Synthesis of Complex Molecules by Intramolecular Ring-opening of Epoxides with Heteronucleophiles

Synthesis of Complex Molecules by Ring-opening of Epoxides with C-Nucleophiles

Epoxy Glycals

Synthesis of Complex Molecules by Rearrangement Reactions of Epoxides

VINYLEPOXIDES IN ORGANIC SYNTHESIS

Synthesis of Vinylepoxides

Transformations of Vinylepoxides

THE BIOSYNTHESIS OF EPOXIDES

Cytochrome P450 Monooxygenases

Flavin-dependent Epoxidases

Dioxygenases

Epoxidation through Dehydrogenation

Dehalogenases

AZIRIDINE NATURAL PRODUCTS - DISCOVERY, BIOLOGICAL ACTIVITY AND BIOSYNTHESIS

Mitomycins and Related Natural Products

The Azinomycins

Other Aziridine Natural Products

EPOXIDES AND AZIRIDINES IN CLICK CHEMISTRY

Epoxides in Click Chemistry

Aziridines in Click Chemistry

Aziridinium Ions in Click Chemistry

ASYMMETRIC SYNTHESIS OF EPOXIDES AND AZIRIDINES FROM ALDEHYDES AND IMINES
Asymmetric Epoxidation of Carbonyl Compounds
Asymmetric Aziridination of Imines
VINYLAZIRIDINES IN ORGANIC SYNTHESIS
Direct Synthesis of Vinylaziridines
Ring-opening Reactions with Nucleophiles
Isomerization Including Rearrangement
Cycloaddition
Electron Transfer to Vinylaziridines
ASYMMETRIC SYNTHESES WITH AZIRIDINECARBOXYLATE AND AZIRIDINEPHOSPHONATE BUILDING BLOCKS
Preparation of Aziridine-2-carboxylates and Aziridine-2-phosphonates
Reactions of Aziridine-2-carboxylates and Aziridine-2-phosphonates
Applications in Natural Product Syntheses
SYNTHESIS OF AZIRIDINES
Overview and General Features
METALATED EPOXIDES AND AZIRIDINES IN SYNTHESIS
Metalated Epoxides
Metalated Aziridines
METAL-CATALYZED SYNTHESIS OF EPOXIDES
Oxidants Available for Selective Transition Metal-catalyzed Epoxidation
Epoxidations of Olefins Catalyzed by Early Transition Metals
Chromium-, Molybdenum-, and Tungsten-catalyzed Epoxidations
Manganese-catalyzed Epoxidations
Rhenium-catalyzed Epoxidations
Iron-catalyzed Epoxidations
Ruthenium-catalyzed Epoxidations
CATALYTIC ASYMMETRIC EPOXIDE RING-OPENING CHEMISTRY
Enantioselective Nucleophilic Addition to Meso-Epoxides
Kinetic Resolution of Racemic Epoxides
Enantioselective Rearrangements of Epoxides
EPOXIDES IN COMPLEX MOLECULE SYNTHESIS
Synthesis of Complex Molecules by Intramolecular Ring-opening of Epoxides with Heteronucleophiles
Synthesis of Complex Molecules by Ring-opening of Epoxides with C-Nucleophiles
Epoxy Glycals
Synthesis of Complex Molecules by Rearrangement Reactions of Epoxides
VINYLEPOXIDES IN ORGANIC SYNTHESIS
Synthesis of Vinylepoxides
Transformations of Vinylepoxides
THE BIOSYNTHESIS OF EPOXIDES
Cytochrome P450 Monooxygenases
Flavin-dependent Epoxidases
Dioxygenases
Epoxidation through Dehydrogenation
Dehalogenases
AZIRIDINE NATURAL PRODUCTS - DISCOVERY, BIOLOGICAL ACTIVITY AND BIOSYNTHESIS
Mitomycins and Related Natural Products
The Azinomycins
Other Aziridine Natural Products
EPOXIDES AND AZIRIDINES IN CLICK CHEMISTRY
Epoxides in Click Chemistry
Aziridines in Click Chemistry
Aziridinium Ions in Click Chemistry

Über Autor(innen)

Professor Andrei K. Yudin obtained his PhD degree at the University of Southern California under the direction of Professors G. K. Surya Prakash and George A. Olah. He then took up a post-doctoral position in the laboratory of Professor K. Barry Sharpless at the Scripps Research Institute. In 1998, he started his independent career at the University of Toronto. His research interests are in transition metal catalysis, development of novel synthetic methods, and synthesis of complex heterocycles of biological significance.