Enantioselective Synthesis of Beta-Amino Acids,9780471467380

Enantioselective Synthesis of Beta-Amino Acids

by ;
Edition: 2nd
ISBN13: 9780471467380
ISBN10: 0471467383
Format: Hardcover
Pub. Date: 2005-04-21
Publisher(s): Wiley-VCH
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Summary

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.

Author Biography

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.

Table of Contents

Preface xiii
Preface to the First Edition xv
Contributors xvii
1. Structural Types of Relevant β-Amino Acid Targets
1(18)
Eusebio Juaristi
1.1 Introduction
1(2)
1.2 β²-Alkyl-β-Amino Acids
3(1)
1.3 β³-Alkyl-β-Amino Acids
3(1)
1.4 β²,²-Disubstituted β-Amino Acids
4(1)
1.5 β²,³-Disubstituted β-Amino Acids
4(1)
1.6 β²,³-Disubstituted β-Amino Acids
5(1)
1.7 β²,²,³-Trisubstituted β-Amino Acids
6(1)
1.8 β²,²,³,³-Tetrasubstituted β-Amino Acids
7(1)
1.9 β²-Aryl-β-Amino Acids
7(1)
1.10 β³-Aryl-β-Amino Acids
7(2)
1.11 Olefinic and Alkynyl-β-Amino Acids
9(2)
1.12 α,β-Diamino Acids
11(1)
1.13 α-Hydroxy-β-Amino Acids
12(1)
1.14 β-Amino-γ-Hydroxy Acids
12(1)
1.15 Carbocyclic β-Amino Acids
13(1)
1.16 Heterocyclic β-Amino Acids
13(1)
References
14(5)
2. β-Amino Acids in Natural Products
19(74)
Peter Spiteller and Franz von Nussbaum
2.1 Introduction
19(4)
2.2 Natural Products Containing β-Amino Acids Related to Proteinogenic α-Amino Acids
23(14)
2.3 Natural Products Containing Unusual Aliphatic β-Amino Acids
37(10)
2.4 Natural Products Containing Aliphatic Hydroxy-β-Amino Acids
47(4)
2.5 Natural Products Containing Aliphatic β-Amino Acids with Oxo Groups
51(2)
2.6 Natural Products Containing Amino-β-Amino Acids (Except β-Lysine)
53(8)
2.7 Alicyclic and Heterocyclic β-Amino Acids
61(3)
2.8 Natural Products Containing Unusual Aromatic β-Amino Acids
64(9)
2.9 Conclusions and Future Prospects
73(2)
References
75(18)
3. Preparation of Enantiopure β-Amino Acids by Homologation of α-Amino Acids
93(14)
Joachim Podlech
3.1 Introduction
93(1)
3.2 Arndt-Eistert Homologation
93(7)
3.3 Homologation of Amino Acids with Concomitant β-Lactam Formation
100(3)
3.4 Homologation of Amino Acids Using Cyano Hydrins
103(1)
References
104(3)
4. Asymmetric Catalysis in Enantioselective Synthesis of β-Amino Acids
107(10)
Anna G. Wenzel and Eric N. Jacobsen
4.1 Introduction
107(1)
4.2 Catalytic Asymmetric Conjugate Addition for Preparation of β-Aliphatic-β-Amino Acids
107(3)
4.3 Asymmetric Mannich Reactions Catalyzed by Thiourea Derivatives for Enantioselective Preparation of β-Aryl-β-Amino Acids
110(4)
References
114(3)
5. Enantioselective Synthesis of Conformationally Constrained β-Amino Acids
117(22)
Rosa M. Ortuño
5.1 General Introduction
117(1)
5.2 Cycloalkane β-Amino Acids
117(10)
5.3 Alkyl-Substituted β-Amino Acids
127(7)
5.4 Other Methodologies
134(3)
References
137(2)
6. Catalytic Enantioselective Mannich Reactions
139(20)
Masaharu Ueno and Shu Kobayashi
6.1 Introduction
139(1)
6.2 Catalytic Enantioselective Mannich Reactions Using Chiral Lewis Acid Catalysts
140(10)
6.3 Catalytic Asymmetric Mannich Reactions via Metal Enolates
150(1)
6.4 Catalytic Asymmetric Reaction Using an Organocatalyst
151(3)
6.5 Miscellaneous
154(1)
References
154(5)
7. Enantioselective Synthesis of β-Amino Acids via Stereoselective Hydrogenation of β-Aminoacrylic Acid Derivatives
159(22)
Eusebio Juaristi, Victor Manuel Gutiérrez-Garcia, and Heraclio López-Ruiz
7.1 Introduction
159(3)
7.2 Recent Developments: Rhodium Complexes with Chiral Phosphorus Bidentate Ligands
162(11)
7.3 Recent Developments: Rhodium Complexes with Chiral Phosphorus Monodentate Ligands
173(1)
7.4 Recent Developments: Ruthenium Complexes with Chiral Phosphorus Bidentate Ligands
174(4)
References
178(3)
8. Asymmetric Synthesis of β-Amino Acids by Enolate Additions to tert-Butanesulfinyl Imines
181(14)
Kristin Brinner and Jonathan A. Ellman
8.1 Introduction
181(1)
8.2 Synthesis of N-tert-Butanesulfinyl 1mines
181(2)
8.3 Synthesis of N-Sulfinyl-Protected β-Amino Acids
183(2)
8.4 N-tert-Butanesulfinyl Protecting Group
185(1)
8.5 Synthetic Utility
186(6)
8.6 Summary
192(1)
References
193(2)
9. Organocatalytic Approaches to Enantioenriched β-Amino Acids
195(20)
Fujie Tanaka and Carlos F. Bathos, III
9.1 Introduction
195(3)
9.2 Mannich-Type Reactions Using Aldehydes and α-Ethyl Glyoxylate
198(1)
9.3 Mannich-Type Reactions Using Aldehydes and Preformed Aldimines
199(3)
9.4 Three-Component Mannich Reactions Using Aldehyde Donors
202(2)
9.5 Proposed Mechanism for L-Proline-Catalyzed Mannich Reactions
204(1)
9.6 Transformation of Product of L-Proline-Catalyzed Mannich Reaction into β-Amino Acid and β-Lactams
204(1)
9.7 One-Pot Transformations via L-Proline-Catalyzed Mannich Reactions Using Aldehydes as Nucleophiles
205(1)
9.8 Mannich Reactions Using α,α-Disubstituted Aldehydes or α-Imidoaldehyde for Preparation of Highly Functionalized β-Amino Acid Derivatives
206(2)
9.9 Other Organocatalytic Reactions for Preparation of Enantioenriched β-Amino Acids
208(3)
9.10 Summary
211(1)
References
212(3)
10. Asymmetric Synthesis of Cyclic β-Amino Acids via Cycloaddition Reactions 215(26)
José Barluenga, Bernardo Olano, Josefa Flórez, and Carlos Valdés
10.1 Introduction
215(1)
10.2 General Strategies in Asymmetric Synthesis of Cyclic β-Amino Acids
216(2)
10.3 Cyclic β-Amino Acids via Cycloaddition Reactions
218(4)
10.4 Synthesis of cis- and trans-2-Aminocyclohexanecarboxylic Acid Derivatives via [4 + 2]-Cycloaddition Reactions
222(5)
10.5 Synthesis of β-Proline Derivatives via [3 + 2]-Cycloaddition Reactions
227(7)
10.6 Synthesis of Constrained Six-Membered Ring α,α-Disubstituted β-Amino Acid Derivatives via [4 + 2]-Cycloaddition Reactions
234(2)
10.7 Summary
236(1)
References
237(4)
11. Enantioselective Synthesis of Novel β-Amino Acids 241(20)
Javed Iqbal and Saibal Kumar Das
11.1 Acyclic Amino Acids
242(12)
11.2 Cyclic and Conformationally Constrained β-Amino Acids
254(3)
11.3 Conclusion
257(2)
References
259(2)
12. Asymmetric Synthesis of Phosphonic Analogs of β-Amino Acids 261(16)
Marian Mikolajczyk, Józef Drabowicz, and Piotr Lyzwa
12.1 Enantioselective C-C Bond-Forming Reactions
262(5)
12.2 Enantioselective C-N Bond-Forming Reactions
267(7)
12.3 Enantioselective C-H Bond-Forming Reactions
274(1)
12.4 Miscellaneous
275(1)
References
276(1)
13. Asymmetric Synthesis of α-Substituted-β-Amino Phosphonates and Phosphinates and β-Amino Sulfur Analogs 277(42)
Francisco Palacios, Concepción Alonso, and Jesús de los Santos
13.1 Introduction
277(1)
13.2 Synthesis of α-Alkyl-β-Amino Phosphorus Derivatives
278(1)
13.3 Synthesis of β-Amino-α-Hydroxy Phosphonic and Phosphinic Acid Derivatives
279(12)
13.4 Synthesis of β-Amino-α-Halogenated Phosphonates
291(1)
13.5 Synthesis of α,β-Diamino Phosphonates and Phosphinates
292(2)
13.6 β-Amino-α-Substituted Phosphorus Derivatives with Peptide Bond Formation: β-Amino-α-Substituted Phosphono- and Phosphinopeptides
294(7)
13.7 β-Amino Sulfur Analogs
301(12)
13.8 Conclusion
313(1)
References
314(5)
14. Stereoselective Synthesis of Fluorine-Containing β-Amino Acids 319(32)
Santos Fustero, Juan F. Sanz-Cervera, and iVadim A. Soloshonok
14.1 Introduction
319(1)
14.2 Acyclic Fluorinated α,β-Disubstituted β-Amino Acids
320(18)
14.3 Cyclic Fluorinated α,β-Disubstituted β-Amino Acids
338(2)
14.4 α-Fluoroalkyl β-Amino Acids
340(3)
14.5 β-Fluoroalkyl β-Amino Acids
343(3)
14.6 β-Substituted α,α-Difluoro-β-Amino Acids
346(3)
References
349(2)
15. Enantioselective Synthesis of β-Amino Acids via Conjugate Addition to α,β-Unsaturated Carbonyl Compounds 351(26)
Scott J. Miller and David J. Guerin
15.1 Introduction
351(1)
15.2 Diastereoselective Additions to Chiral Michael Acceptors
352(4)
15.3 Additions of Chiral Ammonia Equivalents to Michael Acceptors
356(8)
15.4 Methods Based on Asymmetric Catalysis
364(10)
References
374(3)
16. Preparation of Enantiopure β-Amino Acids via Enantioselective Conjugate Addition 377(20)
Mei Liu and Mukund P. Sibi
16.1 Introduction
377(1)
16.2 Conjugate Addition of Alkyl or Aromatic Amines
378(4)
16.3 Addition of Hydroxylamine to Enoates
382(7)
16.4 Conjugate Addition of Azide
389(1)
16.5 Conjugate Addition of Carbon Nucleophiles
390(3)
16.6 Conclusions
393(1)
References
394(3)
17. Biocatalytic Entry to Enantiomerically Pure β-Amino Acids 397(18)
Dmitrii O. Berbasov, Trevor K. Ellis, and Vadim A. Soloshonok
17.1 Introduction
397(1)
17.2 Biocatalytic Entry to Enantiomerically Pure β-Amino Acids
398(15)
17.3 Conclusion
413(1)
References
414(1)
18. Stereoselective Synthesis of β-Amino Acids via Radical Reactions 415(32)
Takeaki Naito and Okiko Miyata
18.1 Introduction
415(2)
18.2 Synthesis of Acyclic β-Amino Acids
417(15)
18.3 Synthesis of Cyclic β-Amino Acids
432(4)
18.4 Synthesis of β-Lactams
436(9)
References
445(2)
19. Recent Advances in Synthesis of α-Hydroxy-β-amino Acids and Their Use in SAR Studies of Taxane Anticancer Agents 447(30)
Jin Chen, Larisa V. Kuznetsova, Maria M. Ungreanu, and Iwao Ojima
19.1 Introduction
447(2)
19.2 Synthesis of Enantiopure α-Hydroxy-β-amino Acid Components of Taxane Anticancer Agents by β-Lactam Synthon Method
449(5)
19.3 New C-13 α-Hydroxy-β-amino Acid Residues and Their Significance in Second-Generation Taxoids
454(11)
19.4 Taxoids with Photoaffinity-Labeled α-Hydroxy-β-amino Acid Residues
465(4)
19.5 Taxoids with Fluorine- and Isotope-Labeled α-Hydroxy-β-amino Acid Residues for NMR Studies
469(1)
19.6 Summary
470(1)
References
471(6)
20. Synthesis of β-Amino Acids and Their Derivatives from β-Lactams: Update 477(20)
Claudio Palomo, Jesús M. Aizpurua, Iñaki Ganboa, and Mikel Oiarbide
20.1 Introduction
477(1)
20.2 β-Lactam Ring Opening by Oxygen Nucleophiles: β-Amino Esters and Related Products
478(6)
20.3 β-Lactam Ring Opening by Nitrogen Nucleophiles: β-Amino Amides and β-Amino Acid-Derived Peptides
484(5)
20.4 β-Lactam Ring Opening by Carbon Nucleophiles: β-Amino Ketones and Related Products
489(2)
20.5 Large-Ring Heterocycles from β-Lactams
491(1)
20.6 Concluding Remarks and Prospects
492(1)
References
493(4)
21. Multiple-Component Condensation Methods for Preparation of Combinatorial Libraries of β-Amino Carbonyl Derivatives 497(30)
James C. Adrian, Jr.
21.1 Introduction
497(3)
21.2 Mannich Reaction
500(13)
21.3 Other Multiple-Component Reactions
513(7)
21.4 Solid-Phase MCC Methods
520(1)
21.5 Conclusions
521(2)
References
523(4)
22. Using Constrained β-Amino Acid Residues to Control β-Peptide Shape and Function 527(66)
Michael A. Gelman and Samuel H. Gellman
22.1 Introduction: β-Peptides in the Foldamer Context
527(4)
22.2 Monomer Synthesis
531(26)
22.3 β-Peptide Synthesis
557(5)
22.4 Conformational Data
562(14)
22.5 Biological Applications
576(8)
22.6 New Frontiers for β-Peptide Structure
584(1)
References
585(8)
23. β²-Amino Acids with Proteinogenic Side Chains and Corresponding Peptides: Synthesis, Secondary Structure, and Biological Activity 593(26)
Marino A. Campo, Jaime Ewa/ante, and Radovan Šehesta
23.1 Introduction
593(1)
23.2 Synthesis of β²-Amino Acids
594(9)
23.3 Solution and Solid-Phase Synthesis of Peptides Containing β²-Amino Acids
603(2)
23.4 Secondary Structures of Peptides Containing β²-Amino Acids
605(6)
23.5 Biologically Active Peptides Containing Proteinogenic β²-Amino Acids
611(3)
23.6 Conclusions
614(1)
Abbreviations
614(1)
References
614(5)
Index 619

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