Enantioselective Synthesis of Beta–Amino Acids

Covers all facets of the synthesis of β–amino acids
As evidenced by an exponential increase in the literature published on the subject, interest in β–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 β–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 β–amino acids. In most cases, the lead chemist who originally developed a method provides an authoritative description of it.
In addition, Enantioselective Synthesis of β–Amino Acids, Second Edition:Features introductory overviews on the structural types of relevant β–amino acid targets and salient β–amino acids present in natural productsDedicates several chapters to advances in the synthesis of oligomers from β–amino acidsIncludes general and practical procedures for the preparation of β–amino acids in each chapterDiscusses the most important methods that have been recently developed for the asymmetric synthesis of cyclic and open–chain β–amino acidsIncludes a report on the preparation of libraries of enantiopure β–amino acids using combinatorial approaches
The only book of its kind available today, Enantioselective Synthesis of β–Amino Acids, Second Edition offers upper–level students and professionals an essential resource for pharmaceutical development, medicinal chemistry, and biochemistry.

Spis treści:
Preface.
Preface to the First Edition.
Contributors.
1. Structural Typ es 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. A symmetric 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 t