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Enantioselective Synthesis of Beta-Amino Acids, 2nd Edition

ISBN: 978-0-471-46738-0
656 pages
April 2005
Enantioselective Synthesis of Beta-Amino Acids, 2nd Edition (0471467383) cover image

Description

Covers all facets of the synthesis of ß-amino acids

As evidenced by an exponential increase in the literature published on the subject, interest in ß-amino acids has grown over the past several years. With major pharmaceutical applications, these amino acids are now studied across multiple lines of research, including combinatorial chemistry, medicinal chemistry, molecular design, proteomics, and others.

This Second Edition of Enantioselective Synthesis of ß-Amino Acids updates reviews included in the First Edition while also covering new developments since its publication. The book presents detailed discussions of the most important methods for the synthesis of ß-amino acids. In most cases, the lead chemist who originally developed a method provides an authoritative description of it.

In addition, Enantioselective Synthesis of ß-Amino Acids, Second Edition:
* Features introductory overviews on the structural types of relevant ß-amino acid targets and salient ß-amino acids present in natural products
* Dedicates several chapters to advances in the synthesis of oligomers from ß-amino acids
* Includes general and practical procedures for the preparation of ß-amino acids in each chapter
* Discusses the most important methods that have been recently developed for the asymmetric synthesis of cyclic and open-chain ß-amino acids
* Includes a report on the preparation of libraries of enantiopure ß-amino acids using combinatorial approaches

The only book of its kind available today, Enantioselective Synthesis of ß-Amino Acids, Second Edition offers upper-level students and professionals an essential resource for pharmaceutical development, medicinal chemistry, and biochemistry.
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Table of Contents

Preface.

Preface to the First Edition.

Contributors.

1. Structural Types of Relevant b-Amino Acid Targets (Eusebio Juaristi).

1.1 Introduction.

1.2 β2-Alkyl-β-Amino Acids.

1.3 β3-Alkyl-β-Amino Acids.

1.4 β2,2-Disubstituted β-Amino Acids.

1.5 β2,3-Disubstituted β-Amino Acids.

1.6 β3,3-Disubstituted β-Amino Acids.

1.7 β2,3,3-Trisubstituted β-Amino Acids.

1.8 β2,2,3,3-Tetrasubstituted β-Amino Acids.

1.9 β2-Aryl-β-Amino Acids.

1.10 β3-Aryl-β-Amino Acids.

1.11 Olefinic and Alkynyl-β-Amino Acids.

1.12 α,β-Diamino Acids.

1.13 α-Hydroxy-β-Amino Acids.

1.14 β-Amino-γ-Hydroxy Acids.

1.15 Carbocyclic β-Amino Acids.

1.16 Heterocyclic β-Amino Acids.

References.

2. β-Amino Acids in Natural Products (Peter Spiteller and Franz von Nussbaum).

2.1 Introduction.

2.2 Natural Products Containing β-Amino Acids Related to Proteinogenic α-Amino Acids.

2.3 Natural Products Containing Unusual Aliphatic β-Amino Acids.

2.4 Natural Products Containing Aliphatic Hydroxy-β-Amino Acids.

2.5 Natural Products Containing Aliphatic β-Amino Acids with Oxo Groups.

2.6 Natural Products Containing Amino-β-Amino Acids (Except β-Lysine).

2.7 Alicyclic and Heterocyclic β-Amino Acids.

2.8 Natural Products Containing Unusual Aromatic β-Amino Acids.

2.9 Conclusions and Future Prospects.

References.

3. Preparation of Enantiopure β-Amino Acids by Homologation of α-Amino Acids (Joachim Podlech).

3.1 Introduction.

3.2 Arndt–Eistert Homologation.

3.3 Homologation of Amino Acids with Concomitant β-Lactam Formation.

3.4 Homologation of Amino Acids Using Cyano Hydrins.

References.

4. Asymmetric Catalysis in Enantioselective Synthesis of β-Amino Acids (Anna G. Wenzel and Eric N. Jacobsen).

4.1 Introduction.

4.2 Catalytic Asymmetric Conjugate Addition for Preparation of β-Aliphatic-β-Amino Acids.

4.3 Asymmetric Mannich Reactions Catalyzed by Thiourea Derivatives for Enantioselective Preparation of β-Aryl-β-Amino Acids.

References.

5. Enantioselective Synthesis of Conformationally Constrained β-Amino Acids (Rosa M. Ortuño).

5.1 General Introduction.

5.2 Cycloalkane β-Amino Acids.

5.3 Alkyl-Substituted β-Amino Acids.

5.4 Other Methodologies.

References.

6. Catalytic Enantioselective Mannich Reactions (Masaharu Ueno and Shū Kobayashi).

6.1 Introduction.

6.2 Catalytic Enantioselective Mannich Reactions Using Chiral Lewis Acid Catalysts.

6.3 Catalytic Asymmetric Mannich Reactions via Metal Enolates.

6.4 Catalytic Asymmetric Reaction Using an Organocatalyst.

6.5 Miscellaneous.

References.

7. Enantioselective Synthesis of β-Amino Acids via Stereoselective Hydrogenation of β-Aminoacrylic Acid Derivatives (Eusebio Juaristi, V&ıacute;ctor Manuel Gutiérrez-Garc&ıacute;a, and Heraclio López-Ruiz)

7.1 Introduction.

7.2 Recent Developments: Rhodium Complexes with Chiral Phosphorus Bidentate Ligands.

7.3 Recent Developments: Rhodium Complexes with Chiral Phosphorus Monodentate Ligands.

7.4 Recent Developments: Ruthenium Complexes with Chiral Phosphorus Bidentate Ligands.

References.

8. Asymmetric Synthesis of β-Amino Acids by Enolate Additions to tert-Butanesulfinyl Imines (Kristin Brinner and Jonathan A. Ellman).

8.1 Introduction.

8.2 Synthesis of N-tert-Butanesulfinyl Imines.

8.3 Synthesis of N-Sulfinyl-Protected β-Amino Acids.

8.4 N-tert-Butanesulfinyl Protecting Group.

8.5 Synthetic Utility.

8.6 Summary.

References.

9. Organocatalytic Approaches to Enantioenriched β-Amino Acids (Fujie Tanaka and Carlos F. Barbas, III).

9.1 Introduction.

9.2 Mannich-Type Reactions Using Aldehydes and α-Ethyl Glyoxylate.

9.3 Mannich-Type Reactions Using Aldehydes and Preformed Aldimines.

9.4 Three-Component Mannich Reactions Using Aldehyde Donors.

9.5 Proposed Mechanism for L-Proline-Catalyzed Mannich Reactions.

9.6 Transformation of Product of L-Proline-Catalyzed Mannich Reaction into β-Amino Acid and β-Lactams.

9.7 One-Pot Transformations via L-Proline-Catalyzed Mannich Reactions Using Aldehydes as Nucleophiles.

9.8 Mannich Reactions Using α,α-Disubstituted Aldehydes or α-Imidoaldehyde for Preparation of Highly Functionalized β-Amino Acid Derivatives.

9.9 Other Organocatalytic Reactions for Preparation of Enantioenriched β-Amino Acids.

9.10 Summary.

References.

10. Asymmetric Synthesis of Cyclic &Beat;-Amino Acids via Cycloaddition Reactions (José Barluenga, Bernardo Olano, Josefa Flórez, and Carlos Valdés).

10.1 Introduction.

10.2 General Strategies in Asymmetric Synthesis of Cyclic β-Amino Acids.

10.3 Cyclic β-Amino Acids via Cycloaddition Reactions.

10.4 Synthesis of cis- and trans-2-Aminocyclohexanecarboxylic Acid Derivatives via [4 + 2]-Cycloaddition Reactions.

10.5 Synthesis of β-Proline Derivatives via [3 + 2]-Cycloaddition Reactions.

10.6 Synthesis of Constrained Six-Membered Ring α,α-Disubstituted β-Amino Acid Derivatives via [4 + 2]-Cycloaddition Reactions.

10.7 Summary.

References.

11. Enantioselective Synthesis of Novel β-Amino Acids (Javed Iqbal and Saibal Kumar Das).

11.1 Acyclic Amino Acids.

11.2 Cyclic and Conformationally Constrained β-Amino Acids.

11.3 Conclusion.

References.

12. Asymmetric Synthesis of Phosphonic Analogs of β-Amino Acids (Marian Mikołajczyk, Józef Drabowicz, and Piotr Lyzwa).

12.1 Enantioselective C–C Bond-Forming Reactions.

12.2 Enantioselective C–N Bond-Forming Reactions.

12.3 Enantioselective C–H Bond-Forming Reactions.

12.4 Miscellaneous.

References.

13. Asymmetric Synthesis of α-Substituted-β-Amino Phosphonates and Phosphinates and β-Amino Sulfur Analogs (Francisco Palacios, Concepción Alonso, and Jesús de los Santos).

13.1 Introduction.

13.2 Synthesis of α-Alkyl-β-Amino Phosphorus Derivatives.

13.3 Synthesis of β-Amino-α-Hydroxy Phosphonic and Phosphinic Acid Derivatives.

13.4 Synthesis of β-Amino-α-Halogenated Phosphonates.

13.5 Synthesis of α, β-Diamino Phosphonates and Phosphinates.

13.6 β-Amino-a-Substituted Phosphorus Derivatives with Peptide Bond Formation: β-Amino-α-Substituted Phosphonoand Phosphinopeptides.

13.7 β-Amino Sulfur Analogs.

13.8 Conclusion.

References.

14. Stereoselective Synthesis of Fluorine-Containing β-Amino Acids (Santos Fustero, Juan F. Sanz-Cervera, and Vadim A. Soloshonok).

14.1 Introduction.

14.2 Acyclic Fluorinated α, β-Disubstituted β-Amino Acids.

14.3 Cyclic Fluorinated α, β-Disubstituted β-Amino Acids.

14.4 a-Fluoroalkyl β-Amino Acids.

14.5 β-Fluoroalkyl β-Amino Acids.

14.6 β-Substituted α, α-Difluoro-β-Amino Acids.

References.

15. Enantioselective Synthesis of β-Amino Acids via Conjugate Addition to α, β-Unsaturated Carbonyl Compounds (Scott J. Miller and David J. Guerin).

15.1 Introduction.

15.2 Diastereoselective Additions to Chiral Michael Acceptors.

15.3 Additions of Chiral Ammonia Equivalents to Michael Acceptors.

15.4 Methods Based on Asymmetric Catalysis.

References.

16. Preparation of Enantiopure β-Amino Acids via Enantioselective Conjugate Addition (Mei Liu and Mukund P. Sibi).

16.1 Introduction.

16.2 Conjugate Addition of Alkyl or Aromatic Amines.

16.3 Addition of Hydroxylamine to Enoates.

16.4 Conjugate Addition of Azide.

16.5 Conjugate Addition of Carbon Nucleophiles.

16.6 Conclusions.

References.

17. Biocatalytic Entry to Enantiomerically Pure β-Amino Acids (Dmitrii O. Berbasov, Trevor K. Ellis, and Vadim A. Soloshonok).

17.1 Introduction.

17.2 Biocatalytic Entry to Enantiomerically Pure β-Amino Acids.

17.3 Conclusion.

References.

18. Stereoselective Synthesis of β-Amino Acids via Radical Reactions (Takeaki Naito and Okiko Miyata).

18.1 Introduction.

18.2 Synthesis of Acyclic β-Amino Acids.

18.3 Synthesis of Cyclic β-Amino Acids.

18.4 Synthesis of β-Lactams.

References.

19. Recent Advances in Synthesis of α-Hydroxy-β-amino Acids and Their Use in SAR Studies of Taxane Anticancer Agents (Jin Chen, Larisa V. Kuznetsova, Ioana M. Ungreanu, and Iwao Ojima).

19.1 Introduction.

19.2 Synthesis of Enantiopure α-Hydroxy-β-amino Acid Components of Taxane Anticancer Agents by β-Lactam Synthon Method.

19.3 New C-13 α-Hydroxy-β-amino Acid Residues and Their Significance in Second-Generation Taxoids.

19.4 Taxoids with Photoaffinity-Labeled α-Hydroxy-β-amino Acid Residues.

19.5 Taxoids with Fluorine- and Isotope-Labeled α-Hydroxy-β-amino Acid Residues for NMR Studies.

19.6 Summary.

References.

20. Synthesis of β-Amino Acids and Their Derivatives from b-Lactams: Update (Claudio Palomo, Jesús M. Aizpurua, Iñaki Ganboa, and Mikel Oiarbide).

20.1 Introduction.

20.2 β-Lactam Ring Opening by Oxygen Nucleophiles: β-Amino Esters and Related Products.

20.3 β-Lactam Ring Opening by Nitrogen Nucleophiles: β-Amino Amides and b-Amino Acid–Derived Peptides.

20.4 β-Lactam Ring Opening by Carbon Nucleophiles: β-Amino Ketones and Related Products.

20.5 Large-Ring Heterocycles from β-Lactams.

20.6 Concluding Remarks and Prospects.

References.

21. Multiple-Component Condensation Methods for Preparation of Combinatorial Libraries of β-Amino Carbonyl Derivatives (James C. Adrian, Jr.).

21.1 Introduction.

21.2 Mannich Reaction.

21.3 Other Multiple-Component Reactions.

21.4 Solid-Phase MCC Methods.

21.5 Conclusions.

References.

22. Using Constrained b-Amino Acid Residues to Control β-Peptide Shape and Function (Michael A. Gelman and Samuel H. Gellman).

22.1 Introduction: β-Peptides in the Foldamer Context.

22.2 Monomer Synthesis.

22.3 β-Peptide Synthesis.

22.4 Conformational Data.

22.5 Biological Applications.

22.6 New Frontiers for β-Peptide Structure.

References.

23. β2-Amino Acids with Proteinogenic Side Chains and Corresponding Peptides: Synthesis, Secondary Structure, and Biological Activity (Marino A. Campo, Jaime Escalante, and Radovan Scaron;ebesta).

23.1 Introduction.

23.2 Synthesis of β2-Amino Acids.

23.3 Solution and Solid-Phase Synthesis of Peptides Containing β2-Amino Acids.

23.4 Secondary Structures of Peptides Containing β2-Amino Acids.

23.5 Biologically Active Peptides Containing Proteinogenic β2-Amino Acids.

23.6 Conclusions.

Abbreviations.

References.

Index.

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Author Information

EUSEBIO JUARISTI is currently Professor of Chemistry at Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Mexico. The author of seven chemistry books, Dr. Juaristi received the Mexican Academy of Sciences Award for Young Scientists in 1988, and the Inter-American Science and Technology Prize of the Organization of American States in 1990. More recently, in 1998, he received the Presidential Medal, the highest recognition for Mexican scientists.

VADIM SOLOSHONOK is a professor in the Department of Chemistry and Biochemistry at the University of Oklahoma.

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Reviews

"…a 'must-have' handbook…it should be on the bookshelves of organic chemists in academia as well as in the pharmaceutical industry." (Journal of the American Chemical Society, October 26, 2005)
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