Modern methods in stereoselective aldol reactions:
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| Language: | English |
| Published: |
Weinheim
Wiley-VCH
2013
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| Subjects: | |
| Online Access: | Inhaltstext Inhaltsverzeichnis |
| Physical Description: | XIV, 536 S. Ill., graph. Darst. 24 cm x 17 cm |
| ISBN: | 9783527332052 |
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| 245 | 1 | 0 | |a Modern methods in stereoselective aldol reactions |c ed. by Rainer Mahrwald |
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IMAGE 1
CONTENTS
PREFACE X I
LIST O F CONTRIBUTORS XIII
1 STEREOSELECTIVE ACETATE ALDOL REACTIONS 1
PEDRO ROMEA AND FELIX URPI 1.1 INTRODUCTION 1
1.2 MUKAIYAMA ALDOL REACTION 2
1.2.1 CONCEPT A N D MECHANISM 2
1.2.2 CHIRAL AUXILIARIES 4
1.2.3 CHIRAL METHYL KETONES 6
1.2.4 CHIRAL ALDEHYDES 8
1.2.4.1 1,2-ASYMMETRIC INDUCTION 8 1.2.4.2 1,3-ASYMMETRIC INDUCTION 13
1.2.4.3 MERGED 1,2-AND 1,3-ASYMMETRIC INDUCTION 17 1.2.5 CHIRAL LEWIS
ACIDS 22
1.2.6 CHIRAL LEWIS BASES 3 5
1.3 METAL ENOLATES 41
1.3.1 CONCEPT A N D MECHANISM 41
1.3.2 CHIRAL AUXILIARIES 4 2
1.3.3 STOICHIOMETRIC LEWIS ACIDS 4 7
1.3.4 CATALYTIC LEWIS ACIDS 48
1.3.5 CHIRAL ALDEHYDES 5 0
1.3.6 CHIRAL METHYL KETONES 5 5
1.3.6.1 A-METHYL KETONES 56 1.3.6.2 A-HYDROXY KETONES 5 7 1.3.6.3
^-HYDROXY KETONES 60 1.3.6.4 F5-HYDROXY A-METHYL KETONES 63 1.3.6.5
A,P-DIHYDROXY KETONES 64 1.3.6.6 REMOTE STEREOCONTROL 6 7 1.4
CONCLUSIONS 6 8
REFERENCES 69
HTTP://D-NB.INFO/1024048241
IMAGE 2
V I | CONTENTS
1 THE VINYLOGOUS MUKAIYAMA ALDOL REACTION IN NATURAL PRODUCT
SYNTHESIS 83 MARTIN CORDES AND MARKUS KALESSE 2.1 INTRODUCTION 83
2.2 ALDEHYDE-DERIVED SILYL DIENOL ETHERS 84 2.2.1 ALDEHYDE-DERIVED SILYL
DIENOL ETHERS - DIASTEREOSELECTIVE PROCESSES 84 2.2.2 ALDEHYDE-DERIVED
SILYL DIENOL ETHERS - ENANTIOSELECTIVE PROCESSES 87 2.3 ESTER-DERIVED
SILYL DIENOL ETHERS 90
2.3.1 ESTER-DERIVED SILYL DIENOL ETHERS - DIASTEREOSELECTIVE PROCESSES
90 2.3.2 ESTER-DERIVED SILYL DIENOL ETHERS - ENANTIOSELECTIVE PROCESSES
96 2.3.3 ESTER-DERIVED SILYL DIENOL ETHERS - ENANTIOSELECTIVE A N D
SUBSTRATE-CONTROLLED PROCESSES 105
2.4 AMIDE-DERIVED SILYL DIENOL ETHERS - VINYLKETENE SILYL N,0-ACETALS
108 2.4.1 MODEL SYSTEMS - KOBAYASHI'S PIONEERING STUDIES 108 2.4.2 TOTAL
SYNTHESES 109
2.5 ACYCLIC ACETOACETATE-DERIVED SILYL DIENOLATES - CHAN'S DIENE 117
2.5.1 CHAN'S DIENE I N DIASTEREOSELECTIVE PROCESSES 117 2.5.2 CHAN'S
DIENE I N ENANTIOSELECTIVE PROCESSES 121 2.5.3 CHAN'S DIENE I N
ENANTIOSELECTIVE A N D SUBSTRATE-CONTROLLED
PROCESSES 122
2.6 CYCLIC ACETOACETATE-DERIVED DIENOLATES 124 2.6.1 CYCLIC
ACETOACETATE-DERIVED DIENOLATES - DIASTEREOSELECTIVE PROCESSES 124 2.6.2
CYCLIC ACETOACETATE-DERIVED DIENOLATES - ENANTIOSELECTIVE
PROCESSES 126
2.6.3 CYCLIC ACETOACETATE-DERIVED DIENOLATES - ENANTIOSELECTIVE A N D
SUBSTRATE-CONTROLLED PROCESSES 132 2.7 FURAN-DERIVED SILYLOXY DIENES 133
2.7.1 FURAN-DERIVED SILYLOXY DIENES - DIASTEREOSELECTIVE PROCESSES 133
2.7.2 FURAN-DERIVED SILYLOXY DIENES - ENANTIOSELECTIVE PROCESSES 138
2.7.3 FURAN-DERIVED SILYLOXY DIENES - ENANTIOSELECTIVE A N D
SUBSTRATE-CONTROLLED PROCESSES 141
2.8 PYRROLE-BASED 2-SILYLOXY DIENES 142 2.9 COMPARISON WITH OTHER
METHODS 148
REFERENCES 151
3 ORGANOCATALYZED ALDOL REACTIONS 155
GABRIELA GUILLENA
3.1 INTRODUCTION 155
3.2 PROLINE AS ORGANOCATALYST 156
3.2.1 INTRAMOLECULAR REACTIONS 156 3.2.1.1 INTRAMOLECULAR PROPOSED
MECHANISM 159 3.2.1.2 APPLICATION TO NATURAL PRODUCT SYNTHESIS 161 3.2.2
I NTERMOLECULAR REACTIONS 163
IMAGE 3
CONTENTS V I I
3.2.2.1 KETONES AS SOURCE O F NUCLEOPHILE 163
3.2.2.2 ALDEHYDES AS SOURCE O F NUCLEOPHILE 171 3.2.2.3 INTERMOLECULAR
REACTION MECHANISM 175 3.2.2.4 APPLICATION TO NATURAL PRODUCT SYNTHESIS
177 3.3 PROLINE DERIVATIVES AS ORGANOCATALYSTS 179 3.3.1 PROLINAMIDE
DERIVATIVES 180 3.3.1.1 KETONES AS SOURCE O F NUCLEOPHILE 180 3.3.1.2
ALDEHYDES AS SOURCE O F NUCLEOPHILE 197 3.3.1.3 APPLICATION TO NATURAL
PRODUCT SYNTHESIS 197 3.3.2 PROLINE PEPTIDE DERIVATIVES 199 3.3.2.1
KETONES AS SOURCE O F NUCLEOPHILE 199 3.3.3 HYDROXYPROLINE DERIVATIVES
205 3.3.3.1 INTRAMOLECULAR REACTIONS 205 3.3.3.2 INTERMOLECULAR
REACTIONS 207
3.3.4 SULFONIMIDE PROLINE DERIVATIVES 216 3.3.4.1 KETONES AS SOURCE O F
NUCLEOPHILE 216 3.3.4.2 APPLICATION TO NATURAL PRODUCT SYNTHESIS 219
3.3.5 OTHER PROLINE DERIVATIVES 220
3.3.5.1 INTRAMOLECULAR REACTIONS 220 3.3.5.2 INTERMOLECULAR REACTIONS
221 3.3.5.3 APPLICATION TO NATURAL PRODUCT SYNTHESIS 231 3.3.6 OTHER
ORGANOCATALYSTS 233
3.3.6.1 INTRAMOLECULAR REACTIONS 233 3.3.6.2 INTERMOLECULAR REACTIONS
235 3.3.7 PHASE-TRANSFER CATALYSIS 251 3.4 CONCLUSIONS A N D OUTLOOK 253
REFERENCES 253
4 SUPERSILYL PROTECTIVE CROUPS IN ALDOL REACTIONS 269
PATRICK B. BRADY AND HISASHI YAMAMOTO 4.1 INTRODUCTION 269
4.2 ALDOL ADDITION WITH ACETALDEHYDE-DERIVED SUPER SILYL ENOL ETHER (1)
270
4.3 A-SUBSTITUTED SILYL ENOL ETHERS DERIVED F R O M ALDEHYDES 270 4.4
ALDOL ADDITION TO CHIRAL ALDEHYDES 272
4.5 ONE-POT SEQUENTIAL ALDOL REACTIONS 274
4.6 SEQUENTIAL ALDOL-ALDOL REACTIONS O F ACETALDEHYDE 275 4.6.1
ACETALDEHYDE DOUBLE ALDOL REACTIONS 275 4.6.2 ACETALDEHYDE TRIPLE ALDOL
REACTIONS 275 4.6.3 MIXED SEQUENTIAL ALDOL-ALDOL REACTIONS 277 4.7
DOUBLE ALDOL REACTIONS WITH A-SUBSTITUTED SILYL ENOL ETHERS 277 4.7.1
SEQUENTIAL ALDOL-ALDOL REACTIONS WITH MIXED SEES 277 4.7.2
PROPIONALDEHYDE ALDOL-ALDOL CASCADE REACTIONS 279 4.7.3 HALOACETALDEHYDE
ALDOL-ALDOL CASCADES 280 4.8 STEREOCHEMICAL CONSIDERATIONS 281
IMAGE 4
V I I I | CONTENTS
4.9 ALDOL REACTIONS O F P-SUPERSILOXY METHYL KETONES 282
4.10 TOTAL SYNTHESIS O F NATURAL PRODUCTS USING SUPERSILYL ALDOL
REACTIONS 285 4.11 CONCLUSION A N D OUTLOOK 288
REFERENCES 288
5 ASYMMETRIC INDUCTION IN ALDOL ADDITIONS 293
LUIZ C. DIAS, ELLEN C. POLO, EMILIO C. DE LUCCA JR, AND MARCO A.B.
FERREIRA 5.1 INTRODUCTION 293
5.2 ASYMMETRIC INDUCTION USING CHIRAL KETONES 295 5.2.1 1,4-ASYMMETRIC
INDUCTION USING A-ALKYL KETONES 296 5.2.2 1,4-ASYMMETRIC INDUCTION USING
A-METHYL-P-BRANCHED KETONES 302 5.2.3 1,4-ASYMMETRIC INDUCTION USING
A-ALKOXY KETONES 305 5.2.4 1,5-ASYMMETRIC INDUCTION USING P-ALKOXY
METHYL KETONES 313 5.2.5 1,6-ASYMMETRIC INDUCTION USING CHIRAL METHYL
KETONES 317 5.3 ASYMMETRIC INDUCTION USING CHIRAL ALDEHYDES 317 5.3.1
1,2-ASYMMETRIC INDUCTION USING CHIRAL ALDEHYDES 317 5.3.2 1,3-ASYMMETRIC
INDUCTION USING CHIRAL ALDEHYDES 335 5.3.3 ASYMMETRIC INDUCTION USING
A-METHYL-P-ALKOXY ALDEHYDES 342
5.3.4 ASYMMETRIC INDUCTION USING A,(3-BISALKOXY ALDEHYDES 357 5.4
ASYMMETRIC INDUCTION I N THE ALDOL ADDITION O F CHIRAL ENOLATES TO
CHIRAL ALDEHYDES 360 REFERENCES 371
6 POLYPROPIONATE SYNTHESIS VIA SUBSTRATE-CONTROLLED STEREOSELECTIVE
ALDOL COUPLINGS O F CHIRAL FRAGMENTS 377 DALE E. WARD
6.1 INTRODUCTION 377
6.2 PRINCIPLES O F STEREOSELECTIVE ALDOL REACTIONS 378 6.2.1 RELATIVE
TOPIRITY 378
6.2.2 CHIRAL REACTANTS 381
6.2.2.1 DIASTEREOFACE SELECTIVITY O F CHIRAL ETHYL KETONES 381 6.2.2.2
DIASTEREOFACE SELECTIVITY O F CHIRAL ALDEHYDES 386 6.2.2.3
MULTIPLICATIVITY RULE 394 6.3 STEREOSELECTIVE ALDOL COUPLING O F CHIRAL
REACTANTS 398
6.3.1 2-ALKOXY-L-METHYLETHYL ETHYL KETONES: PATERSON'S DIPROPIONATE
EQUIVALENT 398 6.3.1.1 REACTIONS WITH ACHIRAL ALDEHYDES 398 6.3.1.2
REACTIONS WITH CHIRAL ALDEHYDES 400 6.3.2 1-METHYLALKYL ETHYL KETONES:
3-DEOXY POLYPROPIONATE EQUIVALENTS 402
6.4 2-ALKOXYALKYL ETHYL KETONES: 2-DESMETHYL POLYPROPIONATE EQUIVALENTS
406 6.4.1 2-ALKOXY-L-METHYLALKYL ETHYL KETONES: POLYPROPIONATE
EQUIVALENTS 409 6.4.1.1 (E) BORON ENOLATES 411 6.4.1.2 (Z) BORON
ENOLATES 412
IMAGE 5
CONTENTS | I X
6.4.1.3 SILYL ENOLATES 413
6.4.1.4 LITHIUM ENOLATES 414 6.4.1.5 TITANIUM ENOLATES 416 6.4.1.6 TIN
ENOLATES 419
6.5 CONCLUSIONS 420
REFERENCES 424
7 APPLICATION O F OXAZOLIDINETHIONES AND THIAZOLIDINETHIONES IN ALDOL
ADDITIONS 431 MICHAEL T. CRIMMINS 7.1 INTRODUCTION 431
7.2 PREPARATION O F OXAZOLIDINETHIONE A N D THIAZOLIDINETHIONE CHIRAL
AUXILIARIES 431 7.3 ACYLATION O F OXAZOLIDINETHIONE A N D
THIAZOLIDINETHIONE CHIRAL AUXILIARIES 433 7.4 PROPIONATE ALDOL ADDITIONS
434
7.5 ACETATE ALDOL ADDITIONS 437
7.6 GLYCOLATE ALDOL ADDITIONS 443
7.6.1 SYNTHETIC APPLICATIONS O F ALDOL ADDITIONS O F N-PROPIONYL
OXAZOLIDINETHIONES A N D THIAZOLIDINETHIONES A N D THEIR SUBSTITUTED
VARIANTS 443
7.6.2 SYNTHETIC APPLICATIONS O F ALDOL ADDITIONS O F
N-ACETYLOXAZOLIDINETHIONES A N D THIAZOLIDINETHIONES 461 7.6.3 SYNTHETIC
APPLICATIONS O F ANTI-ALDOL ADDITIONS OF N-GLYCOLYLOXAZOLIDINETHIONES
466
REFERENCES 471
8 ENZYME-CATALYZED ALDOL ADDITIONS 475
PERT CLAP6S AND JESUS JOGLAR 8.1 INTRODUCTION 475
8.2 PYRUVATE ALDOLASES 477
8.3 N-ACETYLNEURAMINIC ACID ALDOLASE (NEUA) 478 8.3.1 NOVEL NEUA
BIOCATALYST BY PROTEIN ENGINEERING 482 8.3.2 LARGE-SCALE PROCESS 486
8.3.3 RELATED PYRUVATE ALDOLASES/2-OXOBUTYRATE ALDOLASES 487 8.4
DIHYDROXYACETONE PHOSPHATE (DHAP) ALDOLASES 494 8.4.1 STRUCTURE A N D
MECHANISM 500
8.4.2 L-RHAMNULOSE-L-PHOSPHATE ALDOLASE AS A DHA-DEPENDENT ALDOLASE 502
8.5 D-FRUCTOSE-6-PHOSPHATE ALDOLASE A N D TRANSALDOLASE B PHEL78TYR:
FSA-IIKE ALDOLASES 503 8.6 2-DEOXY-D-RIBOSE-5-PHOSPHATE ALDOLASE (RIBA
OR DERA; EC
4.1.2.4) 510
8.7 GLYCINE/ALANINE ALDOLASES 514
8.8 ALDOL REACTIONS CATALYZED BY NON ALDOLASES 520
IMAGE 6
X I CONTENTS
8.9 CONCLUSIONS AND PERSPECTIVES 520
8.9.1 SUBSTRATE TOLERANCE/STEREOSELECTIVITY 521 8.9.2 FUTURE
PERSPECTIVES 521
REFERENCES 522
INDEX 529 |
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| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Modern methods in stereoselective aldol reactions ed. by Rainer Mahrwald Weinheim Wiley-VCH 2013 XIV, 536 S. Ill., graph. Darst. 24 cm x 17 cm txt rdacontent n rdamedia nc rdacarrier Stereoselektive Reaktion (DE-588)4132164-9 gnd rswk-swf Aldolreaktion (DE-588)4324196-7 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Aldolreaktion (DE-588)4324196-7 s Stereoselektive Reaktion (DE-588)4132164-9 s DE-604 Mahrwald, Rainer 1950- Sonstige (DE-588)109693140 oth X:MVB text/html http://deposit.dnb.de/cgi-bin/dokserv?id=4071688&prov=M&dok%5Fvar=1&dok%5Fext=htm Inhaltstext DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025777744&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Modern methods in stereoselective aldol reactions Stereoselektive Reaktion (DE-588)4132164-9 gnd Aldolreaktion (DE-588)4324196-7 gnd |
| subject_GND | (DE-588)4132164-9 (DE-588)4324196-7 (DE-588)4143413-4 |
| title | Modern methods in stereoselective aldol reactions |
| title_auth | Modern methods in stereoselective aldol reactions |
| title_exact_search | Modern methods in stereoselective aldol reactions |
| title_full | Modern methods in stereoselective aldol reactions ed. by Rainer Mahrwald |
| title_fullStr | Modern methods in stereoselective aldol reactions ed. by Rainer Mahrwald |
| title_full_unstemmed | Modern methods in stereoselective aldol reactions ed. by Rainer Mahrwald |
| title_short | Modern methods in stereoselective aldol reactions |
| title_sort | modern methods in stereoselective aldol reactions |
| topic | Stereoselektive Reaktion (DE-588)4132164-9 gnd Aldolreaktion (DE-588)4324196-7 gnd |
| topic_facet | Stereoselektive Reaktion Aldolreaktion Aufsatzsammlung |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=4071688&prov=M&dok%5Fvar=1&dok%5Fext=htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=025777744&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT mahrwaldrainer modernmethodsinstereoselectivealdolreactions |