Preface. <p>Preface to the First Edition.</p> <p>Contributors.</p> <p><b>1. Structural Types of Relevant</b> <b>b</b><b>-Amino Acid Targets</b> (<i>Eusebio Juaristi</i>).</p> <p>1.1 Introduction.</p> <p>1.2 β<sup>2</sup>-Alkyl-β-Amino Acids.</p> <p>1.3 β<sup>3</sup>-Alkyl-β-Amino Acids.</p> <p>1.4 β<sup>2,2</sup>-Disubstituted β-Amino Acids.</p> <p>1.5 β<sup>2,3</sup>-Disubstituted β-Amino Acids.</p> <p>1.6 β<sup>3,3</sup>-Disubstituted β-Amino Acids.</p> <p>1.7 β<sup>2,3,3</sup>-Trisubstituted β-Amino Acids.</p> <p>1.8 β<sup>2,2,3,3</sup>-Tetrasubstituted β-Amino Acids.</p> <p>1.9 β<sup>2</sup>-Aryl-β-Amino Acids.</p> <p>1.10 β<sup>3</sup>-Aryl-β-Amino Acids.</p> <p>1.11 Olefinic and Alkynyl-β-Amino Acids.</p> <p>1.12 α,β-Diamino Acids.</p> <p>1.13 α-Hydroxy-β-Amino Acids.</p> <p>1.14 β-Amino-γ-Hydroxy Acids.</p> <p>1.15 Carbocyclic β-Amino Acids.</p> <p>1.16 Heterocyclic β-Amino Acids.</p> <p>References.</p> <p><b>2. β-Amino Acids in Natural Products</b> (<i>Peter Spiteller and Franz von Nussbaum</i>).</p> <p>2.1 Introduction.</p> <p>2.2 Natural Products Containing β-Amino Acids Related to Proteinogenic α-Amino Acids.</p> <p>2.3 Natural Products Containing Unusual Aliphatic β-Amino Acids.</p> <p>2.4 Natural Products Containing Aliphatic Hydroxy-β-Amino Acids.</p> <p>2.5 Natural Products Containing Aliphatic β-Amino Acids with Oxo Groups.</p> <p>2.6 Natural Products Containing Amino-β-Amino Acids (Except β-Lysine).</p> <p>2.7 Alicyclic and Heterocyclic β-Amino Acids.</p> <p>2.8 Natural Products Containing Unusual Aromatic β-Amino Acids.</p> <p>2.9 Conclusions and Future Prospects.</p> <p>References.</p> <p><b>3. Preparation of Enantiopure β-Amino Acids by Homologation of α-Amino Acids</b> (<i>Joachim Podlech</i>).</p> <p>3.1 Introduction.</p> <p>3.2 Arndt–Eistert Homologation.</p> <p>3.3 Homologation of Amino Acids with Concomitant β-Lactam Formation.</p> <p>3.4 Homologation of Amino Acids Using Cyano Hydrins.</p> <p>References.</p> <p><b>4. Asymmetric Catalysis in Enantioselective Synthesis of β-Amino Acids</b> (<i>Anna G. Wenzel and Eric N. Jacobsen</i>).</p> <p>4.1 Introduction.</p> <p>4.2 Catalytic Asymmetric Conjugate Addition for Preparation of β-Aliphatic-β-Amino Acids.</p> <p>4.3 Asymmetric Mannich Reactions Catalyzed by Thiourea Derivatives for Enantioselective Preparation of β-Aryl-β-Amino Acids.</p> <p>References.</p> <p><b>5. Enantioselective Synthesis of Conformationally Constrained</b> <b>β</b><b>-Amino Acids</b> (<i>Rosa M. Ortuño</i>).</p> <p>5.1 General Introduction.</p> <p>5.2 Cycloalkane β-Amino Acids.</p> <p>5.3 Alkyl-Substituted β-Amino Acids.</p> <p>5.4 Other Methodologies.</p> <p>References.</p> <p><b>6. Catalytic Enantioselective Mannich Reactions</b> (<i>Masaharu Ueno and Shū Kobayashi</i>).</p> <p>6.1 Introduction.</p> <p>6.2 Catalytic Enantioselective Mannich Reactions Using Chiral Lewis Acid Catalysts.</p> <p>6.3 Catalytic Asymmetric Mannich Reactions via Metal Enolates.</p> <p>6.4 Catalytic Asymmetric Reaction Using an Organocatalyst.</p> <p>6.5 Miscellaneous.</p> <p>References.</p> <p><b>7. Enantioselective Synthesis of β-Amino Acids via Stereoselective Hydrogenation of β-Aminoacrylic Acid Derivatives</b> (<i>Eusebio Juaristi, V&ıacute;ctor Manuel Gutiérrez-Garc&ıacute;a, and Heraclio López-Ruiz</i>)</p> <p>7.1 Introduction.</p> <p>7.2 Recent Developments: Rhodium Complexes with Chiral Phosphorus Bidentate Ligands.</p> <p>7.3 Recent Developments: Rhodium Complexes with Chiral Phosphorus Monodentate Ligands.</p> <p>7.4 Recent Developments: Ruthenium Complexes with Chiral Phosphorus Bidentate Ligands.</p> <p>References.</p> <p><b>8. Asymmetric Synthesis of β-Amino Acids by Enolate Additions to</b> <b><i>tert</i></b><b>-Butanesulfinyl Imines</b> (<i>Kristin Brinner and Jonathan A. Ellman</i>).</p> <p>8.1 Introduction.</p> <p>8.2 Synthesis of <i>N-tert</i>-Butanesulfinyl Imines.</p> <p>8.3 Synthesis of <i>N</i>-Sulfinyl-Protected β-Amino Acids.</p> <p>8.4 <i>N-tert</i>-Butanesulfinyl Protecting Group.</p> <p>8.5 Synthetic Utility.</p> <p>8.6 Summary.</p> <p>References.</p> <p><b>9. Organocatalytic Approaches to Enantioenriched</b> <b>β</b><b>-Amino Acids</b> (<i>Fujie Tanaka and Carlos F. Barbas, III</i>).</p> <p>9.1 Introduction.</p> <p>9.2 Mannich-Type Reactions Using Aldehydes and α-Ethyl Glyoxylate.</p> <p>9.3 Mannich-Type Reactions Using Aldehydes and Preformed Aldimines.</p> <p>9.4 Three-Component Mannich Reactions Using Aldehyde Donors.</p> <p>9.5 Proposed Mechanism for <small>L</small>-Proline-Catalyzed Mannich Reactions.</p> <p>9.6 Transformation of Product of <small>L</small>-Proline-Catalyzed Mannich Reaction into β-Amino Acid and β-Lactams.</p> <p>9.7 One-Pot Transformations via <small>L</small>-Proline-Catalyzed Mannich Reactions Using Aldehydes as Nucleophiles.</p> <p>9.8 Mannich Reactions Using α,α-Disubstituted Aldehydes or α-Imidoaldehyde for Preparation of Highly Functionalized β-Amino Acid Derivatives.</p> <p>9.9 Other Organocatalytic Reactions for Preparation of Enantioenriched β-Amino Acids.</p> <p>9.10 Summary.</p> <p>References.</p> <p><b>10. Asymmetric Synthesis of Cyclic &Beat;-Amino Acids via Cycloaddition Reactions</b> (José Barluenga, Bernardo Olano, Josefa Flórez, and Carlos Valdés).</p> <p>10.1 Introduction.</p> <p>10.2 General Strategies in Asymmetric Synthesis of Cyclic β-Amino Acids.</p> <p>10.3 Cyclic β-Amino Acids via Cycloaddition Reactions.</p> <p>10.4 Synthesis of <i>cis</i>- and <i>trans</i>-2-Aminocyclohexanecarboxylic Acid Derivatives via [4 + 2]-Cycloaddition Reactions.</p> <p>10.5 Synthesis of β-Proline Derivatives via [3 + 2]-Cycloaddition Reactions.</p> <p>10.6 Synthesis of Constrained Six-Membered Ring α,α-Disubstituted β-Amino Acid Derivatives via [4 + 2]-Cycloaddition Reactions.</p> <p>10.7 Summary.</p> <p>References.</p> <p><b>11. Enantioselective Synthesis of Novel</b> β<b>-Amino Acids</b> (<i>Javed Iqbal and Saibal Kumar Das</i>).</p> <p>11.1 Acyclic Amino Acids.</p> <p>11.2 Cyclic and Conformationally Constrained β-Amino Acids.</p> <p>11.3 Conclusion.</p> <p>References.</p> <p><b>12. Asymmetric Synthesis of Phosphonic Analogs of β-Amino Acids</b> (<i>Marian Mikołajczyk, Józef Drabowicz, and Piotr Lyzwa</i>).</p> <p>12.1 Enantioselective C–C Bond-Forming Reactions.</p> <p>12.2 Enantioselective C–N Bond-Forming Reactions.</p> <p>12.3 Enantioselective C–H Bond-Forming Reactions.</p> <p>12.4 Miscellaneous.</p> <p>References.</p> <p><b>13. Asymmetric Synthesis of α-Substituted-β-Amino Phosphonates and Phosphinates and β-Amino Sulfur Analogs</b> (<i>Francisco Palacios, Concepción Alonso, and Jesús de los Santos</i>).</p> <p>13.1 Introduction.</p> <p>13.2 Synthesis of α-Alkyl-β-Amino Phosphorus Derivatives.</p> <p>13.3 Synthesis of β-Amino-α-Hydroxy Phosphonic and Phosphinic Acid Derivatives.</p> <p>13.4 Synthesis of β-Amino-α-Halogenated Phosphonates.</p> <p>13.5 Synthesis of α, β-Diamino Phosphonates and Phosphinates.</p> <p>13.6 β-Amino-a-Substituted Phosphorus Derivatives with Peptide Bond Formation: β-Amino-α-Substituted Phosphonoand Phosphinopeptides.</p> <p>13.7 β-Amino Sulfur Analogs.</p> <p>13.8 Conclusion.</p> <p>References.</p> <p><b>14. Stereoselective Synthesis of Fluorine-Containing β-Amino Acids</b> (<i>Santos Fustero, Juan F. Sanz-Cervera, and Vadim A. Soloshonok</i>).</p> <p>14.1 Introduction.</p> <p>14.2 Acyclic Fluorinated α, β-Disubstituted β-Amino Acids.</p> <p>14.3 Cyclic Fluorinated α, β-Disubstituted β-Amino Acids.</p> <p>14.4 a-Fluoroalkyl β-Amino Acids.</p> <p>14.5 β-Fluoroalkyl β-Amino Acids.</p> <p>14.6 β-Substituted α, α-Difluoro-β-Amino Acids.</p> <p>References.</p> <p><b>15. Enantioselective Synthesis of β-Amino Acids via Conjugate Addition to</b> <b>α</b><b>, β-Unsaturated Carbonyl Compounds</b> (<i>Scott J. Miller and David J. Guerin</i>).</p> <p>15.1 Introduction.</p> <p>15.2 Diastereoselective Additions to Chiral Michael Acceptors.</p> <p>15.3 Additions of Chiral Ammonia Equivalents to Michael Acceptors.</p> <p>15.4 Methods Based on Asymmetric Catalysis.</p> <p>References.</p> <p><b>16. Preparation of Enantiopure β-Amino Acids via Enantioselective Conjugate Addition</b> (<i>Mei Liu and Mukund P. Sibi</i>).</p> <p>16.1 Introduction.</p> <p>16.2 Conjugate Addition of Alkyl or Aromatic Amines.</p> <p>16.3 Addition of Hydroxylamine to Enoates.</p> <p>16.4 Conjugate Addition of Azide.</p> <p>16.5 Conjugate Addition of Carbon Nucleophiles.</p> <p>16.6 Conclusions.</p> <p>References.</p> <p><b>17. Biocatalytic Entry to Enantiomerically Pure β-Amino Acids</b> (<i>Dmitrii O. Berbasov, Trevor K. Ellis, and Vadim A. Soloshonok</i>).</p> <p>17.1 Introduction.</p> <p>17.2 Biocatalytic Entry to Enantiomerically Pure β-Amino Acids.</p> <p>17.3 Conclusion.</p> <p>References.</p> <p><b>18. Stereoselective Synthesis of β-Amino Acids via Radical Reactions</b> (Takeaki Naito and Okiko Miyata).</p> <p>18.1 Introduction.</p> <p>18.2 Synthesis of Acyclic β-Amino Acids.</p> <p>18.3 Synthesis of Cyclic β-Amino Acids.</p> <p>18.4 Synthesis of β-Lactams.</p> <p>References.</p> <p><b>19. Recent Advances in Synthesis of α-Hydroxy-β-amino Acids and Their Use in SAR Studies of Taxane Anticancer Agents</b> (<i>Jin Chen, Larisa V. Kuznetsova, Ioana M. Ungreanu, and Iwao Ojima</i>).</p> <p>19.1 Introduction.</p> <p>19.2 Synthesis of Enantiopure α-Hydroxy-β-amino Acid Components of Taxane Anticancer Agents by β-Lactam Synthon Method.</p> <p>19.3 New C-13 α-Hydroxy-β-amino Acid Residues and Their Significance in Second-Generation Taxoids.</p> <p>19.4 Taxoids with Photoaffinity-Labeled α-Hydroxy-β-amino Acid Residues.</p> <p>19.5 Taxoids with Fluorine- and Isotope-Labeled α-Hydroxy-β-amino Acid Residues for NMR Studies.</p> <p>19.6 Summary.</p> <p>References.</p> <p><b>20. Synthesis of β-Amino Acids and Their Derivatives from</b> <b>b</b><b>-Lactams: Update</b> (<i>Claudio Palomo, Jesús M. Aizpurua, Iñaki Ganboa, and Mikel Oiarbide</i>).</p> <p>20.1 Introduction.</p> <p>20.2 β-Lactam Ring Opening by Oxygen Nucleophiles: β-Amino Esters and Related Products.</p> <p>20.3 β-Lactam Ring Opening by Nitrogen Nucleophiles: β-Amino Amides and b-Amino Acid–Derived Peptides.</p> <p>20.4 β-Lactam Ring Opening by Carbon Nucleophiles: β-Amino Ketones and Related Products.</p> <p>20.5 Large-Ring Heterocycles from β-Lactams.</p> <p>20.6 Concluding Remarks and Prospects.</p> <p>References.</p> <p><b>21. Multiple-Component Condensation Methods for Preparation of Combinatorial Libraries of β-Amino Carbonyl Derivatives</b> (<i>James C. Adrian, Jr.</i>).</p> <p>21.1 Introduction.</p> <p>21.2 Mannich Reaction.</p> <p>21.3 Other Multiple-Component Reactions.</p> <p>21.4 Solid-Phase MCC Methods.</p> <p>21.5 Conclusions.</p> <p>References.</p> <p><b>22. Using Constrained</b> <b>b</b><b>-Amino Acid Residues to Control β-Peptide Shape and Function</b> (<i>Michael A. Gelman and Samuel H. Gellman</i>).</p> <p>22.1 Introduction: β-Peptides in the Foldamer Context.</p> <p>22.2 Monomer Synthesis.</p> <p>22.3 β-Peptide Synthesis.</p> <p>22.4 Conformational Data.</p> <p>22.5 Biological Applications.</p> <p>22.6 New Frontiers for β-Peptide Structure.</p> <p>References.</p> <p><b>23. β</b>2<b>-Amino Acids with Proteinogenic Side Chains and Corresponding Peptides: Synthesis, Secondary Structure, and Biological Activity</b> (<i>Marino A. Campo, Jaime Escalante, and Radovan Scaron;ebesta</i>).</p> <p>23.1 Introduction.</p> <p>23.2 Synthesis of β<sup>2</sup>-Amino Acids.</p> <p>23.3 Solution and Solid-Phase Synthesis of Peptides Containing β<sup>2</sup>-Amino Acids.</p> <p>23.4 Secondary Structures of Peptides Containing β<sup>2</sup>-Amino Acids.</p> <p>23.5 Biologically Active Peptides Containing Proteinogenic β<sup>2</sup>-Amino Acids.</p> <p>23.6 Conclusions.</p> <p>Abbreviations.</p> <p>References.</p> <p>Index.</p>