Enantioselective Synthesis of Beta-Amino Acids

659 Pages·2005·4.49 MB·English

by  Eusebio Juaristi

ENANTIOSELECTIVE
SYNTHESIS OF
b-AMINO ACIDS
SECOND EDITION
Edited by
Eusebio Juaristi
Cinvestav-IPN
Mexico
Vadim A. Soloshonok
University of Oklahoma
Norman, Oklahoma
A JOHN WILEY & SONS, INC., PUBLICATION

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
A JOHN WILEY & SONS, INC., PUBLICATION
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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