 The Claisen Rearrangement: Methods and Applications
ISBN: 978-3-527-30825-5
Hardcover
591 pages
April 2007
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List of Contributors.
1 Chorismate-Mutase-Catalyzed Claisen Rearrangement (Hong Guo and Niny Rao).
1.1 Introduction.
1.2 Experimental Studies.
1.3 Catalytic Mechanism of Chorismate Mutase.
1.4 Conclusion.
2 Chiral-Metal-Complex-Catalyzed Aliphatic Claisen Rearrangement (Koichi Mikami and Katsuhiro Akiyama).
2.1 Introduction.
2.2 Binding Modes of Main-group and Late Transition Metals.
2.3 Aluminum(III)-promoted Claisen Rearrangement.
2.4 Copper(II)-catalyzed Claisen Rearrangement.
2.5 Palladium(II)-catalyzed Claisen Rearrangement.
3 Aliphatic and Aromatic Claisen Rearrangement.
3.1 Aliphatic Claisen Rearrangement (Hayato Ichikawa and Keiji Maruoka).
3.1.1 Introduction.
3.1.2 Synthesis of Allyl Vinyl Ethers.
3.1.3 Acyclic Aliphatic Claisen Rearrangement.
3.1.4 Claisen Rearrangement of Cyclic Allyl Vinyl Ethers.
3.1.5 Cyclic Vinyl Ethers.
3.1.6 Cyclic Allyl Ethers.
3.1.7 Tandem Reactions Including Aliphatic Claisen Rearrangement.
3.1.8 The Carbanion-Accelerated Claisen Rearrangement.
3.1.9 Conclusion.
3.2 Aromatic Claisen Rearrangement (Hisanaka Ito and Takeo Taguchi).
3.2.1 Introduction.
3.2.2 Mechanism.
3.2.3 Substrate and Substituent Effect.
3.2.4 Reaction Conditions.
3.2.5 Thio-, Amino-, and Related Claisen Rearrangement.
3.2.6 Asymmetric Synthesis.
3.2.7 Synthetic Applications.
4 The Ireland–Claisen Rearrangement (1972–2004) (Christopher M. McFarland and Matthias C. McIntosh).
4.1 Introduction.
4.2 History.
4.3 Numbering and Nomenclature.
4.4 Rearrangement Temperature, Substituent Effects and Catalysis.
4.5 Transition State Structure.
4.6 Stereochemical Aspects.
4.7 Methods of Ketene Acetal Formation.
4.8 Structural Variations in Allylic Esters.
4.9 Applications to Natural Product Synthesis.
4.10 Propargyl Esters.
4.11 Conclusion.
5 Simple and Chelate Enolate Claisen Rearrangement.
5.1 Simple Enolate Claisen Rearrangement (Mukund G. Kulkarni).
5.1.1 Introduction.
5.1.2 History.
5.1.3 Simple Enolates of Allylic Esters.
5.1.4 Stereoselectivity in Enolate Formation.
5.1.5 Simple Enolates of Allylic Esters of a-Hetero Acids.
5.1.6 Simple Enolates of N-Allyl Amides.
5.1.7 Miscellaneous Enolates.
5.1.8 Conclusion.
5.2 Chelate Enolate Claisen Rearrangement (Uli Kazmaier).
5.2.1 Introduction.
5.2.2 Claisen Rearrangements of Substrates with Chelating Substituents in the a-Position.
5.2.3 Claisen Rearrangements of Substrates Bearing Chelating Substituents in the β-Position.
5.2.4 Chelation Controlled Aza-Claisen Rearrangements.
6 Claisen–Johnson Orthoester Rearrangement (Yves Langlois).
6.1 Introduction.
6.2 Historical Overview.
6.3 Mechanistic Aspects.
6.4 Synthetic Applications.
6.5 Conclusion.
7 The Meerwein–Eschenmoser–Claisen Rearrangement (Stefan N. Gradl and Dirk Trauner).
7.1 Definition, Discovery and Scope.
7.2 Formation of Ketene N,O-Acetals.
7.3 Selectivity.
7.4 Applications in Synthesis.
8 The Carroll Rearrangement (Mark A. Hatcher and Gary H. Posner).
8.1 Introduction.
8.2 Mechanism.
8.3 Synthetic Applications.
8.4 Carroll Variants.
8.5 Conclusion.
9 Thio-Claisen Rearrangement (Stéphane Perrio, Vincent Reboul, Carole Alayrac, and Patrick Metzner).
9.1 Introduction.
9.2 Basic Versions.
9.3 Rearrangement with Stereochemical Control.
9.4 Applications in Organic Synthesis.
9.5 Conclusion.
10 Aza-Claisen Rearrangement (Udo Nubbemeyer).
10.1 Introduction.
10.2 Aromatic Simple Aza-Claisen Rearrangements.
10.3 Aliphatic Simple Aza-Claisen Rearrangements.
10.4 Amide Acetal and Amide Enolate Claisen Rearrangements.
10.5 Zwitterionic Aza-Claisen Rearrangements.
10.6 Alkyne Aza-Claisen Rearrangements.
10.7 Iminoketene Claisen Rearrangements.
11 Mechanistic Aspects of the Aliphatic Claisen Rearrangement (Julia Rehbein and Martin Hiersemann).
References.
Subject Index.
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