Enantioselective Synthesis of ?-Amino Acids, Second Edition

642 Pages·2005·5.52 MB·English

ENANTIOSELECTIVE
SYNTHESIS OF
b-AMINO ACIDS
ENANTIOSELECTIVE
SYNTHESIS OF
b-AMINO ACIDS
SECOND EDITION
Edited by
Eusebio Juaristi
Cinvestav-IPN
Mexico
Vadim A. Soloshonok
University of Oklahoma
Norman, Oklahoma
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LibraryofCongressCataloging-in-PublicationData:
Enantioselectivesynthesisofb-aminoacids/editedbyEusebioJuaristiand
VadimA.Soloshonok.–2nded.
p. cm.
Includesindex.
ISBN0-471-46738-3(cloth)
1.bLactamantibiotics–Synthesis. 2.Aminoacids–Synthesis. 3.Chiraldrugs–Synthesis.
4.Enantiomers–Synthesis. I.Juaristi,Eusebio. II.Soloshonok,V.A.
RS431.B48E52 2005
6150.19–dc22 2004010498
PrintedintheUnitedStatesofAmerica
10987654321
CONTENTS
Preface xiii
Preface to the First Edition xv
Contributors xvii
1. Structural Types of Relevant b-Amino Acid Targets 1
EusebioJuaristi
1.1 Introduction 1
1.2 b2-Alkyl-b-Amino Acids 3
1.3 b3-Alkyl-b-Amino Acids 3
1.4 b2,2-Disubstituted b-Amino Acids 4
1.5 b2,3-Disubstituted b-Amino Acids 4
1.6 b3,3-Disubstituted b-Amino Acids 5
1.7 b2,2,3-Trisubstituted b-Amino Acids 6
1.8 b2,2,3,3-Tetrasubstituted b-Amino Acids 7
1.9 b2-Aryl-b-Amino Acids 7
1.10 b3-Aryl-b-Amino Acids 7
1.11 Olefinic and Alkynyl-b-Amino Acids 9
1.12 a,b-Diamino Acids 11
1.13 a-Hydroxy-b-Amino Acids 12
1.14 b-Amino-g-Hydroxy Acids 12
1.15 Carbocyclic b-Amino Acids 13
1.16 Heterocyclic b-Amino Acids 13
References 14
2. b-Amino Acids in Natural Products 19
Peter SpitellerandFranz vonNussbaum
2.1 Introduction 19
2.2 Natural Products Containing b-Amino Acids Related to
Proteinogenic a-Amino Acids 23
2.3 Natural Products Containing Unusual Aliphatic b-Amino Acids 37
2.4 Natural Products Containing Aliphatic Hydroxy-b-Amino Acids 47
2.5 Natural Products Containing Aliphatic b-Amino Acids
with Oxo Groups 51
v
vi CONTENTS
2.6 Natural Products Containing Amino-b-Amino Acids
(Except b-Lysine) 53
2.7 Alicyclic and Heterocyclic b-Amino Acids 61
2.8 Natural Products Containing Unusual Aromatic
b-Amino Acids 64
2.9 Conclusions and Future Prospects 73
References 75
3. Preparation of Enantiopure b-Amino Acids by
Homologation of a-Amino Acids 93
JoachimPodlech
3.1 Introduction 93
3.2 Arndt–Eistert Homologation 93
3.3 Homologation of Amino Acids with Concomitant
b-Lactam Formation 100
3.4 Homologation of Amino Acids Using Cyano Hydrins 103
References 104
4. Asymmetric Catalysis in Enantioselective Synthesis of
b-Amino Acids 107
AnnaG.Wenzel andEricN.Jacobsen
4.1 Introduction 107
4.2 Catalytic Asymmetric Conjugate Addition for Preparation
of b-Aliphatic-b-Amino Acids 107
4.3 Asymmetric Mannich Reactions Catalyzed by Thiourea
Derivatives for Enantioselective Preparation of
b-Aryl-b-Amino Acids 110
References 114
5. Enantioselective Synthesis of Conformationally
Constrained b-Amino Acids 117
RosaM.Ortun˜o
5.1 General Introduction 117
5.2 Cycloalkane b-Amino Acids 117
5.3 Alkyl-Substituted b-Amino Acids 127
5.4 Other Methodologies 134
References 137
6. Catalytic Enantioselective Mannich Reactions 139
MasaharuUenoandShu¯ Kobayashi
6.1 Introduction 139
6.2 Catalytic Enantioselective Mannich Reactions
Using Chiral Lewis Acid Catalysts 140
CONTENTS vii
6.3 Catalytic Asymmetric Mannich Reactions via Metal Enolates 150
6.4 Catalytic Asymmetric Reaction Using an Organocatalyst 151
6.5 Miscellaneous 154
References 154
7. Enantioselective Synthesis of b-Amino Acids via Stereoselective
Hydrogenation of b-Aminoacrylic Acid Derivatives 159
EusebioJuaristi, V´ıctorManuelGutie´rrez-Garc´ıa,
andHeraclioLo´pez-Ruiz
7.1 Introduction 159
7.2 Recent Developments: Rhodium Complexes with
Chiral Phosphorus Bidentate Ligands 162
7.3 Recent Developments: Rhodium Complexes with
Chiral Phosphorus Monodentate Ligands 173
7.4 Recent Developments: Ruthenium Complexes with
Chiral Phosphorus Bidentate Ligands 174
References 178
8. Asymmetric Synthesis of b-Amino Acids by Enolate Additions
to tert-Butanesulfinyl Imines 181
KristinBrinnerandJonathanA.Ellman
8.1 Introduction 181
8.2 Synthesis of N-tert-Butanesulfinyl Imines 181
8.3 Synthesis of N-Sulfinyl-Protected b-Amino Acids 183
8.4 N-tert-Butanesulfinyl Protecting Group 185
8.5 Synthetic Utility 186
8.6 Summary 192
References 193
9. Organocatalytic Approaches to Enantioenriched b-Amino Acids 195
FujieTanakaandCarlosF.Barbas,III
9.1 Introduction 195
9.2 Mannich-Type Reactions Using Aldehydes and
a-Ethyl Glyoxylate 198
9.3 Mannich-Type Reactions Using Aldehydes and
Preformed Aldimines 199
9.4 Three-Component Mannich Reactions Using
Aldehyde Donors 202
9.5 Proposed Mechanism for L-Proline-Catalyzed
Mannich Reactions 204
9.6 Transformation of Product of L-Proline-Catalyzed Mannich
Reaction into b-Amino Acid and b-Lactams 204
9.7 One-Pot Transformations via L-Proline-Catalyzed Mannich
Reactions Using Aldehydes as Nucleophiles 205
viii CONTENTS
9.8 Mannich Reactions Using a,a-Disubstituted Aldehydes
or a-Imidoaldehyde for Preparation of Highly
Functionalized b-Amino Acid Derivatives 206
9.9 Other Organocatalytic Reactions for Preparation of
Enantioenriched b-Amino Acids 208
9.10 Summary 211
References 212
10. Asymmetric Synthesis of Cyclic b-Amino Acids via
Cycloaddition Reactions 215
Jose´ Barluenga, BernardoOlano,JosefaFlo´rez,andCarlosValde´s
10.1 Introduction 215
10.2 General Strategies in Asymmetric Synthesis of Cyclic
b-Amino Acids 216
10.3 Cyclic b-Amino Acids via Cycloaddition Reactions 218
10.4 Synthesis of cis- and trans-2-Aminocyclohexanecarboxylic
Acid Derivatives via [4þ2]-Cycloaddition Reactions 222
10.5 Synthesis of b-Proline Derivatives via [3þ2]-Cycloaddition
Reactions 227
10.6 Synthesis of Constrained Six-Membered Ring
a,a-Disubstituted b-Amino Acid Derivatives via
[4þ2]-Cycloaddition Reactions 234
10.7 Summary 236
References 237
11. Enantioselective Synthesis of Novel b-Amino Acids 241
JavedIqbalandSaibalKumarDas
11.1 Acyclic Amino Acids 242
11.2 Cyclic and Conformationally Constrained b-Amino Acids 254
11.3 Conclusion 257
References 259
12. Asymmetric Synthesis of Phosphonic Analogs of
b-Amino Acids 261
MarianMikołajczyk, Jo´zef Drabowicz,andPiotrLyz˙wa
12.1 Enantioselective C–C Bond-Forming Reactions 262
12.2 Enantioselective C–N Bond-Forming Reactions 267
12.3 Enantioselective C–H Bond-Forming Reactions 274
12.4 Miscellaneous 275
References 276
13. Asymmetric Synthesis of a-Substituted-b-Amino Phosphonates
and Phosphinates and b-Amino Sulfur Analogs 277
FranciscoPalacios,Concepcio´n Alonso,andJesu´sdelosSantos
13.1 Introduction 277
CONTENTS ix
13.2 Synthesis of a-Alkyl-b-Amino Phosphorus Derivatives 278
13.3 Synthesis of b-Amino-a-Hydroxy Phosphonic and
Phosphinic Acid Derivatives 279
13.4 Synthesis of b-Amino-a-Halogenated Phosphonates 291
13.5 Synthesis of a,b-Diamino Phosphonates and Phosphinates 292
13.6 b-Amino-a-Substituted Phosphorus Derivatives with Peptide
Bond Formation: b-Amino-a-Substituted Phosphono-
and Phosphinopeptides 294
13.7 b-Amino Sulfur Analogs 301
13.8 Conclusion 313
References 314
14. Stereoselective Synthesis of Fluorine-Containing
b-Amino Acids 319
SantosFustero,JuanF.Sanz-Cervera,andVadimA.Soloshonok
14.1 Introduction 319
14.2 Acyclic Fluorinated a,b-Disubstituted b-Amino Acids 320
14.3 Cyclic Fluorinated a,b-Disubstituted b-Amino Acids 338
14.4 a-Fluoroalkyl b-Amino Acids 340
14.5 b-Fluoroalkyl b-Amino Acids 343
14.6 b-Substituted a,a-Difluoro-b-Amino Acids 346
References 349
15. Enantioselective Synthesis of b-Amino Acids via Conjugate
Addition to a,b-Unsaturated Carbonyl Compounds 351
ScottJ.MillerandDavidJ.Guerin
15.1 Introduction 351
15.2 Diastereoselective Additions to Chiral Michael Acceptors 352
15.3 Additions of Chiral Ammonia Equivalents
to Michael Acceptors 356
15.4 Methods Based on Asymmetric Catalysis 364
References 374
16. Preparation of Enantiopure b-Amino Acids
via Enantioselective Conjugate Addition 377
MeiLiuandMukundP.Sibi
16.1 Introduction 377
16.2 Conjugate Addition of Alkyl or Aromatic Amines 378
16.3 Addition of Hydroxylamine to Enoates 382
16.4 Conjugate Addition of Azide 389
16.5 Conjugate Addition of Carbon Nucleophiles 390
16.6 Conclusions 393
References 394
x CONTENTS
17. Biocatalytic Entry to Enantiomerically Pure
b-Amino Acids 397
DmitriiO.Berbasov,TrevorK.Ellis,andVadimA.Soloshonok
17.1 Introduction 397
17.2 Biocatalytic Entry to Enantiomerically Pure b-Amino Acids 398
17.3 Conclusion 413
References 414
18. Stereoselective Synthesis of b-Amino Acids via
Radical Reactions 415
TakeakiNaitoandOkikoMiyata
18.1 Introduction 415
18.2 Synthesis of Acyclic b-Amino Acids 417
18.3 Synthesis of Cyclic b-Amino Acids 432
18.4 Synthesis of b-Lactams 436
References 445
19. Recent Advances in Synthesis of a-Hydroxy-b-amino Acids
and Their Use in SAR Studies of Taxane Anticancer Agents 447
JinChen,LarisaV.Kuznetsova,IoanaM.Ungreanu,andIwaoOjima
19.1 Introduction 447
19.2 Synthesis of Enantiopure a-Hydroxy-b-amino Acid Components
of Taxane Anticancer Agents by b-Lactam Synthon Method 449
19.3 New C-13 a-Hydroxy-b-amino Acid Residues and
Their Significance in Second-Generation Taxoids 454
19.4 Taxoids with Photoaffinity-Labeled a-Hydroxy-b-amino
Acid Residues 465
19.5 Taxoids with Fluorine- and Isotope-Labeled
a-Hydroxy-b-amino Acid Residues for NMR Studies 469
19.6 Summary 470
References 471
20. Synthesis of b-Amino Acids and Their Derivatives
from b-Lactams: Update 477
ClaudioPalomo,Jesu´sM.Aizpurua,In˜akiGanboa,andMikel Oiarbide
20.1 Introduction 477
20.2 b-Lactam Ring Opening by Oxygen Nucleophiles:
b-Amino Esters and Related Products 478
20.3 b-Lactam Ring Opening by Nitrogen Nucleophiles:
b-Amino Amides and b-Amino Acid–Derived Peptides 484
20.4 b-Lactam Ring Opening by Carbon Nucleophiles:
b-Amino Ketones and Related Products 489
20.5 Large-Ring Heterocycles from b-Lactams 491
CONTENTS xi
20.6 Concluding Remarks and Prospects 492
References 493
21. Multiple-Component Condensation Methods for
Preparation of Combinatorial Libraries of
b-Amino Carbonyl Derivatives 497
JamesC.Adrian,Jr.
21.1 Introduction 497
21.2 Mannich Reaction 500
21.3 Other Multiple-Component Reactions 513
21.4 Solid-Phase MCC Methods 520
21.5 Conclusions 521
References 523
22. Using Constrained b-Amino Acid Residues to Control
b-Peptide Shape and Function 527
MichaelA.GelmanandSamuelH.Gellman
22.1 Introduction: b-Peptides in the Foldamer Context 527
22.2 Monomer Synthesis 531
22.3 b-Peptide Synthesis 557
22.4 Conformational Data 562
22.5 Biological Applications 576
22.6 New Frontiers for b-Peptide Structure 584
References 585
23. b2-Amino Acids with Proteinogenic Side Chains and
Corresponding Peptides: Synthesis, Secondary Structure,
and Biological Activity 593
MarinoA.Campo,JaimeEscalante, andRadovanSˇebesta
23.1 Introduction 593
23.2 Synthesis of b2-Amino Acids 594
23.3 Solution and Solid-Phase Synthesis of Peptides Containing
b2-Amino Acids 603
23.4 Secondary Structures of Peptides Containing b2-Amino Acids 605
23.5 Biologically Active Peptides Containing Proteinogenic
b2-Amino Acids 611
23.6 Conclusions 614
Abbreviations 614
References 614
Index 619