Amino Acids, Peptides and Proteins in Organic Chemistry Volume 1

Amino Acids, Peptides and Proteins in Organic Chemistry
 
Author:
Andrew B. Hughes
Publisher: Wiley-VCH
ISBN No: 978-3-527-32096-7
Release at: 2009
Pages: 708
Edition:
Volume 1 - Origins and Synthesis of Amino Acids
File Size: 5 MB
File Type: pdf
Language: English



Content of Amino Acids, Peptides and Proteins in Organic Chemistry



Part One Origins of Amino Acids 1
1 Extraterrestrial Amino Acids 3
Z. Martins and M.A. Sephton
1.1 Introduction 3
1.2 ISM 6
1.2.1 Formation of Amino Acids in the ISM via Solid-Phase Reactions 6
1.2.2 Formation of Amino Acids in the ISM via Gas-Phase Reactions 8
1.3 Comets 9
1.4 Meteorites 11
1.4.1 Sources of Meteoritic Amino Acids (Extraterrestrial versus
Terrestrial Contamination) 17
1.4.1.1 Detection of Amino Acids that are Unusual in the Terrestrial
Environment 17
1.4.1.2 Determination of the Amino Acid Content of the Meteorite Fall
Environment 17
1.4.1.3 Determination of Enantiomeric Ratios 18
1.4.1.4 Determination of Compound-Specific Stable Isotope Ratios
of Hydrogen, Carbon, and Nitrogen 18
1.4.2 Synthesis of Meteoritic Amino Acids 19
1.5 Micrometeorites and IDPs 23
1.6 Mars 23
1.7 Delivery of Extraterrestrial Amino Acid to the Earth and its
Importance to the Origin of Life 24
1.8 Conclusions 26
References 27
2 ‘‘Terrestrial’’ Amino Acids and their Evolution 43
Stephen Freeland
2.1 Introduction 43
2.2 What are the 20 ‘‘Terrestrial’’ Amino Acids? 44
2.2.1 The 21st and 22nd Genetically Encoded Amino Acids 45
2.2.2 Do other Genetically Encoded Amino Acids Await Discovery? 46
2.2.3 Genetic Engineering can Enlarge the Amino Acid Alphabet 47
2.2.4 Significance of Understanding the Origins of the
Standard Alphabet 48
2.3 What do We Know about the Evolution of the Standard Amino
Acid Alphabet? 49
2.3.1 Nonbiological, Natural Synthesis of Amino Acids 50
2.3.2 Biosynthetic Theories for the Evolutionary Expansion of the
Standard Amino Acid Alphabet 53
2.3.3 Evidence for a Smaller Initial Amino Acid Alphabet 55
2.3.4 Proteins as Emergent Products of an RNA World 56
2.3.5 Stereochemical Rationale for Amino Acid Selection 57
2.4 Amino Acids that Life Passed Over: A Role for
Natural Selection? 58
2.4.1 Were the Standard Amino Acids Chosen for High
Biochemical Diversity? 60
2.4.2 Were the Standard Amino Acids Chosen for ‘‘Cheap’’
Biosynthesis? 62
2.4.3 Were the Standard Amino Acids Chosen to Speed Up Evolution? 62
2.5 Why Does Life Genetically Encode L-Amino Acids? 64
2.6 Summary, Synthesis, and Conclusions 64
References 66
Part Two Production/Synthesis of Amino Acids 77
3 Use of Enzymes in the Synthesis of Amino Acids 79
Theo Sonke, Bernard Kaptein, and Hans E. Schoemaker
3.1 Introduction 79
3.2 Chemo-Enzymatic Processes to Enantiomerically Pure
Amino Acids 80
3.3 Acylase Process 81
3.4 Amidase Process 83
3.4.1 Amidase Process for a,a-Disubstituted a-Amino Acids 86
3.5 Hydantoinase Process 88
3.6 Ammonia Lyase Processes 90
3.6.1 Aspartase-Catalyzed Production of L-Aspartic Acid 91
3.6.2 Production of L-Alanine from Fumaric Acid by
an Aspartase–Decarboxylase Cascade 92
3.6.3 Phenylalanine Ammonia Lyase-Catalyzed Production of
L-Phenylalanine and Derivatives 93
3.7 Aminotransferase Process 94
3.7.1 Aminotransferase-Catalyzed Production of D-a-H-a-Amino Acids 97
3.8 AADH Process 99
3.9 Conclusions 102
References 103
4 b-Amino Acid Biosynthesis 119
Peter Spiteller
4.1 Introduction 119
4.1.1 Importance of b-Amino Acids and their Biosynthesis 119
4.1.2 Scope of this Chapter 119
4.2 Biosynthesis of b-Amino Acids 120
4.2.1 Biosynthesis of b-Alanine and b-Aminoisobutyric Acid 120
4.2.1.1 b-Alanine 120
4.2.1.2 b-Aminoisobutyric Acid 122
4.2.2 Biosynthesis of b-Amino Acids by 2,3-Aminomutases from
a-Amino Acids 122
4.2.2.1 b-Lysine, b-Arginine, and Related b-Amino Acids 124
4.2.2.2 b-Phenylalanine, b-Tyrosine, and Related b-Amino Acids 127
4.2.2.3 b-Glutamate and b-Glutamine 132
4.2.2.4 b-Leucine 132
4.2.2.5 b-Alanine 132
4.2.3 Biosynthesis of a,b-Diamino Acids from a-Amino Acids 132
4.2.3.1 General Biosynthesis of a,b-Diamino Acids 132
4.2.3.2 Structures and Occurrence of a,b-Diamino Acids in Nature 132
4.2.3.3 Biosynthesis of Selected a,b-Diamino Acids 135
4.2.3.3.1 Biosynthesis of b-ODAP 135
4.2.3.3.2 Biosynthesis of the a,b-Diaminopropanoic Acid Moiety in the
Bleomycins 136
4.2.3.3.3 Biosynthesis of the Penicillins 137
4.2.3.3.4 Biosynthesis of the Capreomycidine Moiety in Viomycine 137
4.2.3.3.5 Biosynthesis of the Streptolidine Moiety in Streptothricin F 137
4.2.4 Biosynthesis of a-Keto-b-Amino Acids from a-Amino Acids 139
4.2.5 De Novo Biosynthesis of b-Amino Acids by PKSs 139
4.2.5.1 Introduction 139
4.2.5.2 General Biosynthesis of Polyketide-Type b-Amino Acids 141
4.2.5.3 Structures and Occurrence of Polyketide-Type b-Amino Acids
in Nature 142
4.2.5.4 Biosynthesis of Selected Polyketide-Type b-Amino Acids 149
4.2.5.4.1 Long-Chain b-Amino Acids Occurring as Constituents of
the Iturins 149
4.2.5.4.2 Biosynthesis of the Ahda Moiety in Microginin 151
4.2.5.4.3 Biosynthesis of the Ahpa Residue in Bestatin 151
4.2.5.4.4 Biosynthesis of the Adda Residue in the Microcystins 152
4.2.6 b-Amino Acids Whose Biosynthesis is Still Unknown 152
4.3 Conclusions and Future Prospects 154
References 155
5 Methods for the Chemical Synthesis of Noncoded a-Amino
Acids found in Natural Product Peptides 163
Stephen A. Habay, Steve S. Park, Steven M. Kennedy,
and A. Richard Chamberlin
5.1 Introduction 163
5.2 Noncoded CAAs 164
5.3 Noncoded Amino Acids by Chemical Modification of Coded
Amino Acids 185
5.4 Noncoded Amino Acids with Elaborate Side-Chains 205
5.5 Conclusions 226
References 226
6 Synthesis of N-Alkyl Amino Acids 245
Luigi Aurelio and Andrew B. Hughes
6.1 Introduction 245
6.2 N-Methylation via Alkylation 246
6.2.1 SN2 Substitution of a-Bromo Acids 246
6.2.2 N-Methylation of Sulfonamides, Carbamates, and Amides 249
6.2.2.1 Base-Mediated Alkylation of N-Tosyl Sulfonamides 249
6.2.2.2 Base Mediated Alkylation of N-Nitrobenzenesulfonamides 250
6.2.2.3 N-Methylation via Silver Oxide/Methyl Iodide 252
6.2.2.4 N-Methylation via Sodium Hydride/Methyl Iodide 253
6.2.2.5 N-Methylation of Trifluoroacetamides 257
6.2.2.6 N-Methylation via the Mitsunobu Reaction 257
6.3 N-Methylation via Schiff s Base Reduction 259
6.3.1 Reduction of Schiff s Bases via Transition
Metal-Mediated Reactions 259
6.3.2 Reduction of Schiffs Bases via Formic Acid: The Leuckart
Reaction 260
6.3.3 Quaternization of Imino Species 261
6.3.4 Reduction of Schiffs Bases via Borohydrides 263
6.3.5 Borane Reduction of Amides 264
6.4 N-Methylation by Novel Methods 265
6.4.1 1,3-Oxazolidin-5-ones 265
6.4.2 Asymmetric Syntheses 272
6.4.3 Racemic Syntheses 277
6.5 N-Alkylation of Amino Acids 280
6.5.1 Borohydride Reduction of Schiff s Bases 280
6.5.1.1 Sodium Borohydride Reductions 281
6.5.1.2 Sodium Cyanoborohydride Reductions 281
6.5.1.3 Sodium Triacetoxyborohydride Reductions 282
6.5.2 N-Alkylation of Sulfonamides 282
6.5.2.1 Base-Mediated Alkylation of Benzene Sulfonamides 282
6.5.3 Reduction of N-Acyl Amino Acids 283
6.5.3.1 Reduction of Acetamides 284
6.5.4 Novel Methods for N-Alkylating a-Amino Acids 284
6.5.4.1 Asymmetric Synthesis of N-Alkyl a-Amino Acids 284
6.5.4.2 N-Alkylation of 1,3-Oxazolidin-5-ones 284
References 286
7 Recent Developments in the Synthesis of b-Amino Acids 291
Yamir Bandala and Eusebio Juaristi
7.1 Introduction 291
7.2 Synthesis of b-Amino Acids by Homologation of a-Amino Acids 291
7.3 Chiral Pool: Enantioselective Synthesis of b-Amino Acids from
Aspartic Acid, Asparagine, and Derivatives 298
7.4 Synthesis of b-Amino Acids by Conjugate Addition of Nitrogen
Nucleophiles to Enones 300
7.4.1 Achiral b-Amino Acids 300
7.4.2 Enantioselective Approaches 304
7.4.2.1 Addition of ‘‘Chiral Ammonia’’ Equivalents to Conjugated
Prochiral Acceptors 304
7.4.2.2 Addition of a Nitrogen Nucleophile to a Chiral Acceptor 306
7.4.2.3 Asymmetric Catalysis 308
7.5 Synthesis of b-Amino Acids via 1,3-Dipolar Cycloaddition 312
7.6 Synthesis of b-Amino Acids by Nucleophilic Additions 316
7.6.1 Aldol- and Mannich-Type Reactions 316
7.6.2 Morita–Baylis–Hillman-Type Reactions 321
7.6.3 Mannich-Type Reactions 324
7.7 Synthesis of b-Amino Acids by Diverse Addition or
Substitution Reactions 328
7.8 Synthesis of b-Amino Acids by Stereoselective Hydrogenation
of Prochiral 3-Aminoacrylates and Derivatives 330
7.8.1 Reductions Involving Phosphorus-Metal Complexes 331
7.8.2 Reductions Involving Catalytic Hydrogenations 333
7.9 Synthesis of b-Amino Acids by use of Chiral Auxiliaries:
Stereoselective Alkylation 334
7.10 Synthesis of b-Amino Acids via Radical Reactions 338
7.11 Miscellaneous Methods for the Synthesis of b-Amino Acids 340
7.12 Conclusions 347
7.13 Experimental Procedures 348
7.13.1 Representative Experimental Procedure: Synthesis of (S)-
3-(tert-Butyloxycarbonylamino)-4-phenylbutanoic Acid 348
7.13.2 Representative Experimental Procedure: Synthesis of
(S)-2-(Aminomethyl)-4-phenylbutanoic Acid, (S)-19 350
7.13.3 Representative Experimental Procedure: Synthesis of b3-Amino Acids
by Conjugate Addition of Homochiral Lithium N-Benzyl-N-
(a-methylbenzyl)amide 352
7.13.4 Representative Experimental Procedure: Synthesis of Cyclic and
Acyclic b-Amino Acid Derivatives by 1,3-Dipolar Cycloaddition 353
7.13.5 Representative Experimental Procedure: Synthesis of (R)-3-tert-
Butoxycarbonylamino-3-phenylpropionic Acid Isopropyl Ester using
a Mannich-Type Reaction 354
7.13.6 Representative Experimental Procedure: General Procedure for the
Hydrogenation of (Z)- and (E)-b-(Acylamino) acrylates by Chiral
Monodentate Phosphoramidite Ligands 354
7.13.7 Representative Experimental Procedure: Synthesis of Chiral
a-Substituted b-Alanine 355
7.13.8 Representative Experimental Procedure: Synthesis of Chiral b-Amino
Acids by Diastereoselective Radical Addition to Oxime Esters 357
References 358
8 Synthesis of Carbocyclic b-Amino Acids 367
Loránd Kiss, Enik}o Forró, and Ferenc Fülöp
8.1 Introduction 367
8.2 Synthesis of Carbocyclic b-Amino Acids 368
8.2.1 Synthesis of Carbocyclic b-Amino Acids via Lithium Amide-Promoted
Conjugate Addition 369
8.2.2 Synthesis of Carbocyclic b-Amino Acids by Ring-Closing
Metathesis 371
8.2.3 Syntheses from Cyclic b-Keto Esters 372
8.2.4 Cycloaddition Reactions: Application in the Synthesis of Carbocyclic
b-Amino Acids 375
8.2.5 Synthesis of Carbocyclic b-Amino Acids from Chiral Monoterpene
b-Lactams 377
8.2.6 Synthesis of Carbocyclic b-Amino Acids by Enantioselective
Desymmetrization of meso Anhydrides 378
8.2.7 Miscellaneous 379
8.2.8 Synthesis of Small-Ring Carbocyclic b-Amino Acid
Derivatives 383
8.3 Synthesis of Functionalized Carbocyclic b-Amino Acid
Derivatives 385
8.4 Enzymatic Routes to Carbocyclic b-Amino Acids 393
8.4.1 Enantioselective N-Acylations of b-Amino Esters 394
8.4.2 Enantioselective O-Acylations of N-Hydroxymethylated b-Lactams 394
8.4.3 Enantioselective Ring Cleavage of b-Lactams 395
8.4.4 Biotransformation of Carbocyclic Nitriles 396
8.4.5 Enantioselective Hydrolysis of b-Amino Esters 396
8.4.6 Analytical Methods for the Enantiomeric Separation of Carbocyclic
b-Amino Acids 397
8.5 Conclusions and Outlook 398
8.6 Experimental Procedures 399
8.6.1 Synthesis of Hydroxy Amino Ester Ethyl (1R,2S,4S)-2-(Benzyloxycarbonylamino)-4-hydroxycyclohexanecarboxylate (205a)
by Oxirane Ring Opening of with Sodium Borohydride 399
8.6.2 Synthesis of Bicyclic b-Lactam (1R,5S)-6-azabicyclo[3.2.0]hept-3-
en-7-one (223) by the Addition of Chlorosulfonyl Isocyanate
to Cyclopentadiene 399
8.6.3 Synthesis of b-Amino Ester Ethyl cis-2-aminocyclopent-
3-enecarboxylate Hydrochloride (223a) by Lactam Ring-Opening Reaction of Azetidinone 223 400
8.6.4 Synthesis of Epoxy Amino Ester Ethyl (1R,2R,3R,5S)-2-(tert-butoxycarbonylamino)-6-oxabicyclo[3.1.0]hexane-3-carboxylate (225) by Epoxidation of Amino Ester 224 400
8.6.5 Synthesis of Azido Ester Ethyl (1R,2R,3R,4R)-4-Azido-2- (tert-butoxycarbonylamino)-3-hydroxycyclopentanecarboxylate (229)
by Oxirane Ring Opening of with Sodium Azide 401
8.6.6 Isomerization of Azido Amino Ester to Ethyl (1S,2R,3R,4R)-4-Azido-2-(tert-butoxycarbonylamino)-3-hydroxycyclopentanecarboxylate (230) 401
8.6.7 Lipase-Catalyzed Enantioselective Ring Cleavage of 4,5-Benzo-7-
azabicyclo[4.2.0]octan-8-one (271), Synthesis of (1R,2R)- and
(1S,2S)-1-Amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic Acid
Hydrochlorides (307 and 308) 402
8.6.8 Lipase-Catalyzed Enantioselective Hydrolysis of Ethyl trans-2-
aminocyclohexane-1-carboxylate (298), Synthesis of (1R,2R)- and
(1S,2S)-2-Aminocyclohexane-1-carboxylic Acid Hydrochlorides
(309 and 310) 404
References 405
9 Synthetic Approaches to a,b-Diamino Acids 411
Alma Viso and Roberto Fernández de la Pradilla
9.1 Introduction 411
9.2 Construction of the Carbon Backbone 411
9.2.1 Methods for the Formation of the Cb–Cc Bond 411
9.2.1.1 Reaction of Glycinates and Related Nucleophiles with Electrophiles 411
9.2.1.2 Dimerization of Glycinates 416
9.2.1.3 Through Cyclic Intermediates 417
9.2.2 Methods in Which the Ca–Cb Bond is Formed 420
9.2.2.1 Nucleophilic Synthetic Equivalents of CO2R 420
9.2.2.2 Electrophilic Synthetic Equivalents of CO2R and Other Approaches 423
9.2.3 Methods in Which the CbCb0 or CcCc0 Bonds are Formed 424
9.3 Introduction of the Nitrogen Atoms in the Carbon Backbone 425
9.3.1 From Readily Available a-Amino Acids 425
9.3.2 From Allylic Alcohols and Amines 427
9.3.3 From Halo Alkanoates 428
9.3.4 From Alkenoates 429
9.3.5 Electrophilic Amination of Enolates and Related Processes 431
9.3.6 From b-Keto Esters and Related Compounds 433
9.4 Conclusions 433
9.5 Experimental Procedures 434
9.5.1 (SS,2R,3S)-(þ)-Ethyl-2-N-(diphenylmethyleneamino)-3-N-(p-toluenesul-
finyl)-amino-3-phenylpropanoate (14b) 434
9.5.2 Synthesis of Ethyl (2R,3R)-3-amino-2-(4-methoxyphenyl)
aminopentanoate 32a via Asymmetric aza-Henry Reaction 434
References 435
10 Synthesis of Halogenated a-Amino Acids 441
Madeleine Strickland and Christine L. Willis
10.1 Introduction 441
10.2 Halogenated Amino Acids with a Hydrocarbon Side-Chain 442
10.2.1 Halogenated Alanines and Prolines 442
10.2.2 Halogenated a-Amino Acids with Branched Hydrocarbon
Side-Chains 445
10.2.2.1 Halogenated Valines and Isoleucines 445
10.2.2.2 Halogenated Leucines 451
10.3 Halogenated Amino Acids with an Aromatic Side-Chain 457
10.3.1 Halogenated Phenylalanines and Tyrosines 457
10.3.2 Halogenated Histidines 460
10.3.3 Halogenated Tryptophans 462
10.4 Halogenated Amino Acids with Heteroatoms in the Aliphatic
Side-Chain 463
10.4.1 Halogenated Aspartic and Glutamic Acids 463
10.4.2 Halogenated Threonine and Lysine 465
References 466
11 Synthesis of Isotopically Labeled a-Amino Acids 473
Caroline M. Reid and Andrew Sutherland
11.1 Introduction 473
11.2 Enzyme-Catalyzed Methods 473
11.3 Chiral Pool Approach 477
11.4 Chemical Asymmetric Methods 483
11.5 Conclusions 488
11.6 Experimental Procedures 489
11.6.1 Biocatalysis: Synthesis of [15N]L-amino Acids from a-Keto Esters
using a One-Pot Lipase-Catalyzed Hydrolysis and Amino Acid
Dehydrogenase-Catalyzed Reductive Amination 489
11.6.2 Chiral Pool: Preparation of Aspartic Acid Semi-Aldehydes as Key
Synthetic Intermediates; Synthesis of Methyl (2S)-N,N-di-tert-
butoxycarbonyl-2-amino-4-oxobutanoate from L-aspartic Acid 489
11.6.3 Asymmetric Methods: Asymmetric Alkylation Using the Williams
Oxazine and Subsequent Hydrogenation to Give the
a-Amino Acid 490
References 491
12 Synthesis of Unnatural/Nonproteinogenic a-Amino Acids 495
David J. Ager
12.1 Introduction 495
12.2 Chemical Methods 497
12.2.1 Resolution Approaches 497
12.2.2 Side-Chain Methods 497
12.2.2.1 Introduction of the Side-Chain 497
12.2.2.2 Modifications of the Side-Chain 500
12.2.3 Introduction of Functionality 502
12.2.3.1 Nitrogen Introduction 502
12.2.3.2 Carboxylic Acid Introduction 503
12.2.3.2.1 Strecker Reaction 503
12.2.4 Hydrogenation 504
12.2.5 Other Chemical Methods 508
12.3 Enzymatic Methods 508
12.3.1 Acylases 509
12.3.2 Hydantoinases 510
12.3.3 Ammonia Lyases 510
12.3.4 Transaminases 511
12.3.5 Dehydrogenases 513
12.3.6 Amino Acid Oxidases 514
12.3.7 Decarboxylases 515
12.4 Conclusions 516
12.5 Experimental Procedures 516
12.5.1 Side-Chain Introduction with a Phase-Transfer Catalyst 516
12.5.2 Introduction of Nitrogen Through an Oxazolidinone Enolate
with a Nitrogen Electrophile 517
12.5.3 Asymmetric Hydrogenation with Knowles Catalyst 518
12.5.4 Asymmetric Hydrogenation with Rh(DuPhos) Followed by Enzyme-
Catalyzed Inversion of the a-Center 519
References 520
13 Synthesis of g- and d-Amino Acids 527
Andrea Trabocchi, Gloria Menchi, and Antonio Guarna
13.1 Introduction 527
13.2 g-Amino Acids 528
13.2.1 GABA Analogs 528
13.2.2 a- and b-Hydroxy-g-Amino Acids 534
13.2.3 Alkene-Derived g-Amino Acids 539
13.2.4 SAAs 541
13.2.5 Miscellaneous Approaches 542
13.3 d-Amino Acids 547
13.3.1 SAAs 547
13.3.1.1 Furanoid d-SAA 547
13.3.1.2 Pyranoid d-SAA 552
13.3.2 d-Amino Acids as Reverse Turn Mimetics 554
13.3.3 d-Amino Acids for PNA Design 562
13.3.4 Miscellaneous Examples 564
13.4 Conclusions 566
References 567
14 Synthesis of g-Aminobutyric Acid Analogs 573
Jane R. Hanrahan and Graham A.R. Johnston
14.1 Introduction 573
14.2 a-Substituted g-Amino Acids 575
14.3 b-Substituted g-Amino Acids 579
14.3.1 Pregabalin 581
14.3.2 Gabapentin 584
14.3.3 Baclofen and Analogs 584
14.4 g-Substituted g-Amino Acids 592
14.4.1 Vigabatrin 597
14.5 Halogenated g-Amino Acids 599
14.6 Disubstituted g-Amino Acids 600
14.6.1 a,b-Disubstituted g-Amino Acids 600
14.6.2 a,g-Disubstituted g-Amino Acids 601
14.6.3 b,b-Disubstituted g-Amino Acids 604
14.6.4 b,g-Disubstituted g-Amino Acids 604
14.7 Trisubstituted g-Amino Acids 604
14.8 Hydroxy-g-Amino Acids 605
14.8.1 a-Hydroxy-g-Amino Acids 605
14.8.2 b-Hydroxy-g-Amino Acids 606
14.8.3 a-Hydroxy-g-Substituted g-Amino Acids 619
14.8.4 b-Hydroxy-g-Substituted g-Amino Acids 619
14.8.5 b-Hydroxy-Disubstituted g-Amino Acids 638
14.9 Unsaturated g-Amino Acids 640
14.9.1 Unsaturated Substituted g-Amino Acids 641
14.10 Cyclic g-Amino Acids 644
14.10.1 Cyclopropyl g-Amino Acids 644
14.10.2 Cyclobutyl g-Amino Acids 648
14.10.3 Cyclopentyl g-Amino Acids 653
14.10.4 Cyclohexyl g-Amino Acids 663
14.11 Conclusions 666
14.12 Experimental Procedures 666
14.12.1 (R)-2-Ethyl-4-nitrobutan-1-ol (36c) 666
14.12.2 N-tert-Butyl-N-(p-chlorophenylethyl) a-Diazoacetamide 669
14.12.3 (R )-5-[(1-Oxo-2-(tert-butoxycarbonylamino)-3-phenyl)-propyl]-2,2-
dimethyl-1,3-dioxane-4,6-dione 670
14.12.4 (R )- and (S)-[2-(Benzyloxy) ethyl]oxirane 671
14.12.5 Dimethyl (S,S)-(–)-3-N,N-bis(a-Methylbenzyl)-amino-2-
oxopropylphosphonate 672
14.12.6 Boc-L-leucinal 673
14.12.7 Cross-Coupling of N-tert-Butylsulfinyl Imine and tert-Butyl
3-oxopropanoate 674
14.12.8 (10S,4S)-4-Bromomethyl-1-(1-phenyleth-1-yl)-pyrrolidin-2-one 675
14.12.9 (þ)-(R,S)-4-Amino-2-cyclopentene-1-carboxylic Acid 676
References 677
Index 691

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