Alpha-amino acid derivatives and alpha-fluoro ketones by enantioselective decarboxylation:
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
2003
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | Regensburg, Univ., Diss., 2003 |
| Beschreibung: | 98 Bl. graph. Darst. |
Internformat
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| 100 | 1 | |a Baur, Markus A. |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Alpha-amino acid derivatives and alpha-fluoro ketones by enantioselective decarboxylation |c presented by Markus A. Baur |
| 264 | 1 | |c 2003 | |
| 300 | |a 98 Bl. |b graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Regensburg, Univ., Diss., 2003 | ||
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| 650 | 0 | 7 | |a Fluororganische Verbindungen |0 (DE-588)4154846-2 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Asymmetrische Synthese |0 (DE-588)4135603-2 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Aminosäurederivate |0 (DE-588)4324626-6 |2 gnd |9 rswk-swf |
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Datensatz im Suchindex
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TABLE OF CONTENTS
1 INTRODUCTION 1
1.1 CHIRALITY 1
1.2 CHIRAL SWITCH 2
1.3 ENANTIOSELECTIVE CATALYSIS 4
2 GENERAL PART 6
2.1 ENANTIOSELECTIVE DECARBOXYLATION 6
2.2 PROTONATION OF ENOLIC SPECIES 9
2.3 CINCHONA ALKALOIDS AS CATALYSTS 12
3 SYNTHESIS 15
3.1 GOALS OF THIS STUDY 15
3.2 SYNTHESIS OF SUBSTRATES FOR THE ENANTIOSELECTIVE DECARBOXYLATION 16
3.2.1 2-AF-ACETYLAMINO-2-ALKYLMALONIC ACID MONOETHYL ESTERS 16
3.2.2 SYNTHESIS OF A-FLUORINATED P-KETO ESTERS 17
3.2.2.1 SYNTHESIS OF BENZYL P-KETO ESTERS 17
3.2.2.2 FLUORINATION OF P-KETO ESTERS 18
3.2.3 SYNTHESIS OF 2-FLUORO-L-TETRALOL 19
3.3 SYNTHESIS OF THE CATALYSTS 20
3.3.1 SYNTHESIS OF AMIDES OF 9-AMINO(9-DEOXY)EPICINCHONINE 20
3.3.2 FURTHER DERI VATIVES 21
3.3.2.1 DERIVATIVES OF 9-AMINO(9-DEOXY)EPICINCHONINE 21
3.3.2.2 DERIVATIVES OF CINCHONINE 22
3.3.2.3 DERIVATIVE OF QUINIDINE 22
3.3.3 'H NMR ANALYTICS 23
4 CATALYSIS 26
4.1 OVERVIEW ON THE APPLIED CATALYSTS 26
4.2 ENANTIOSELECTIVE DECARBOXYLATION LEADING TO A-AMINO ACID DERIVATIVES
28
4.2.1 GENERAL STANDARD PROCEDURE 28
4.2.2 THE ALANINE SYSTEM 28
4.2.2.1 FIRST TESTINGS 28
4.2.2.2 SCREENING OF BASES 29
4.2.2.3 FURTHER VARIATIONS 32
4.2.2.4 KINETIC STUDY 32
4.2.3 THE VALINE SYSTEM 33
4.2.4 THE PHENYLALANINE SYSTEM 34
4.2.5 ANALYTICS 35
4.3 ENANTIOSELECTIVE DECARBOXYLATION LEADING TO A-FLUORO KETONES 37
4.3.1 GENERAL STANDARD PROCEDURE 38
4.3.2 THE 2-FLUORO-1,2-DIPHENYLETHANONE SYSTEM 38
BIBLIOGRAFISCHE INFORMATIONEN
HTTP://D-NB.INFO/968781632
TABLE OF CONTENTS
4.3.3 DEFLUORINATION OF A-FLUORO KETONES 39
4.3.4 THE 2-FLUORO-CYCLOHEXANONE SYSTEM 42
4.3.5 THE 2-FLUORO-L-TETRALONE SYSTEM 42
4.3.5.1 TESTING OF DIFFERENT PD CATALYSTS 42
4.3.5.2 TESTING OF DIFFERENT CHIRAL BASES 43
4.3.6.3 VARIATIONS WITH QUININE 45
4.3.6.4 FURTHER TESTINGS 46
4.3.6 ANALYTICS 47
5 EXPERIMENTAL PART 49
5.1 GENERAL 49
5.1.1 WORKING CONDITIONS 49
5.1.2 ANALYTICS 50
5.2 SUBSTRATES FOR THE A-AMINO ACID SYSTEM 52
5.2.1 PREPARATION OF 2-/V-ACETYLAMINO-2-ETHOXYCARBONYLPROPIONIC ACID (1)
52
5.2.1.1 DIETHYL 2-V-ACETYLAMINO-2-METHYLMALONATE (14) 52
5.2.1.2 2-A
R-ACETYLAMINO-2-ETHOXYCARBONYLPROPIONIC ACID (1) 52
5.2.2 PREPARATION OF 2-/V-ACETYLAMINO-2-ETHOXYCARBONYL-3-METHYLBUTYRIC
ACID (2) 53
5.2.2.1 DIETHYL 2-V-ACETYLAMINO-2-ISOPROPYLMALONATE (15) 53
5.2.2.2 2-V-ACETYLAMINO-2-ETHOXYCARBONYL-3-METHYLBUTYRIC ACID (2) 54
5.2.3 PREPARATION OF 2-IV-ACETYLAMINO-2-ETHOXYCARBONYL-3-PHENYLPROPIONIC
ACID (3)55
5.2.3.1 DIETHYL 2-A-ACETYLAMINO-2-BENZYLMALONATE (16) 55
5.2.3.2 2-V-ACETYLAMINO-2-ETHOXYCARBONYL-3-PHENYLPROPIONIC ACID (3) 55
5.3 SUBSTRATES FOR THE A-FLUORO KETONE SYSTEM 57
5.3.1 BENZYL 2-FLUORO-3-OXO-2,3-DIPHENYLPROPIONATE (7) 57
5.3.1.1 BENZYL PHENYLACETATE (18) 57
5.3.1.2 BENZYL 3-OXO-2,3-DIPHENYLPROPIONATE (19) 57
5.3.1.3 BENZYL 2-FLUORO-3-OXO-2,3-DIPHENYLPROPIONATE (7) 58
5.3.2 BENZYL 2-FLUOROCYCLOHEXANONE-2-CARBOXYLATE (9) 59
5.3.2.1 ETHYL CYCLOHEXANONE-2-CARBOXYLATE (21) 59
5.3.2.2 BENZYL CYCLOHEXANONE-2-CARBOXYLATE (22) 59
5.3.2.3 BENZYL 2-FLUOROCYCLOHEXANONE-2-CARBOXYLATE (9) 60
5.3.3 BENZYL 2-FLUORO-L-TETRALONE-2-CARBOXYLATE (11) 61
5.3.3.1 ETHYL L-TETRALONE-2-CARBOXYLATE (24) 61
5.3.3.2 BENZYL L-TETRALONE-2-CARBOXYLATE (25) 62
5.3.3.3 BENZYL 2-FLUORO-L-TETRALONE-2-CARBOXYLATE (11) 62
5.3.4 2-FLUORO-L-TETRALOL (27) 63
5.4 SYNTHESIS OF THE CATALYSTS 65
5.4.1 9-AMINO(9-DEOXY)EPICINCHONINE (29) 65
5.4.2 GENERAL PROCEDURE FOR THE SYNTHESIS OF THE AMIDES OF 9-AMINO(9-
DEOXY)EPICINCHONINE (29) 66
5.4.2.1 V-(9-DEOXYEPICINCHONINE-9-YL)BENZAMIDE (30) 67
5.4.2.2 A,/V'-BIS(9-DEOXYEPICINCHONINE-9-YL)ISOPHTHALAMIDE (31) 68
5.4.2.3 A-(9-DEOXYEPICINCHONINE-9-YL)-2-METHOXYBENZAMIDE
(32)
69
5.4.2.4 A-(9-DEOXYEPICINCHONINE-9-YL)-3-METHOXYBENZAMIDE (33) 70
5.4.2.5 IY-(9-DEOXYEPICINCHONINE-9-YL)-4-METHOXYBENZAMIDE
(34)
71
5.4.2.6 7V-(9-DEOXYEPICINCHONINE-9-YL)-3,5-DI-TERT-BUTYLBENZAMIDE (35)
72
TABLE OF CONTENTS
5.4.
2
.7 N-^-DEOXYEPICINCHONINE^-YLTS.S-DIFLUOROBENZAMIDE (36)
73
5.4.2.8 AK9-DEOXYEPICINCHONINE-9-YL)-3,5-DIMETHOXYBENZAMIDE (37) 74
5.4.2.9 IV-(9-DEOXYEPICINCHONINE-9-YL)-3,5-DINITROBENZAMIDE (38)
75
5.4.2.10 IV-(9-DEOXYEPICINCHONINE-9-YL)-4-/CR/-BUTYLBENZAMIDE (39) 76
5.4.2.11 N-(9-DEOXYEPICINCHONINE-9-YL)-ADAMANTANECARBOXAMIDE
(40)
77
5.4.3 FURTHER CINCHONA ALKALOID DERIVATIVES 78
5.4.3
.1
IV-(9-DEOXYEPICINCHONINE-9-YL)-4-METHYLBENZENESULFONAMIDE (
43
)
78
5.4.3
.2
AR-(9-DEOXYEPICINCHONINE-9-YL)-3,5-DI-/CRT-BUTYLBENZENE-
SULFONAMIDE
(44)
79
5.4.3.2.1 3,5-DI-TERT-BUTYLBENZENESULFONYL CHLORIDE (40)
79
5.4.3.2.2 IV-(9-DEOXYEPICINCHONINE-9-YL)-3,5-DI-RERT-BUTYLBENZENE-
SULFONAMIDE (44) 80
5.4.3.3 ;V-(9-DEOXYEPICINCHONINE-9-YL)-2,4-DINITROPHENYLAMINE (
45
) 81
5.4.3.4 /7-(9-DEOXYEPICINCHONINE-9-YL)-JV'-PHENYLUREA
(46)
82
5.4.3.5 CINCHONINE-9-YL PHENYLCARBAMATE (47) 83
5.4.3
.6
CINCHONINE-9-YL 3,5-DI-/ER/-BUTYLBENZENESULFONATE (48) 84
5.4.3.7
(3R,8R,9S)
10,11 -DIHYDRO-3,9-EPOXY-6'-HYDROXYCINCHONANE (50) 85
5.5 CATALYSIS
86
5.5.1 THE AMINO ACID SYSTEMS
86
5.5.1.1 GENERAL STANDARD PROCEDURE
86
5.5.1.2 CHARACTERISATION OF THE PRODUCTS
86
5.5.1.2.1 ETHYL JV-ACETYLALANINATE (4)
86
5.5.1.2.2 ETHYL N-ACETYLVALINATE (5) 87
5.5.1.2.3 ETHYL IV-ACETYLPHENYLALANINATE (
6
) 87
5.5.2 THE 2-FLUORO-L-TETRALONE (12) SYSTEM
88
6 SUMMARY 90
7 ZUSAMMENFASSUNG 92
8 LITERATURE
94 |
| any_adam_object | 1 |
| author | Baur, Markus A. |
| author_facet | Baur, Markus A. |
| author_role | aut |
| author_sort | Baur, Markus A. |
| author_variant | m a b ma mab |
| building | Verbundindex |
| bvnumber | BV017394808 |
| classification_rvk | VH 5075 |
| ctrlnum | (OCoLC)163120465 (DE-599)BVBBV017394808 |
| discipline | Chemie / Pharmazie |
| format | Book |
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| genre | (DE-588)4113937-9 Hochschulschrift gnd-content |
| genre_facet | Hochschulschrift |
| id | DE-604.BV017394808 |
| illustrated | Illustrated |
| indexdate | 2024-11-22T17:38:04Z |
| institution | BVB |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-010481301 |
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| open_access_boolean | |
| owner | DE-355 DE-BY-UBR DE-12 |
| owner_facet | DE-355 DE-BY-UBR DE-12 |
| physical | 98 Bl. graph. Darst. |
| publishDate | 2003 |
| publishDateSearch | 2003 |
| publishDateSort | 2003 |
| record_format | marc |
| spelling | Baur, Markus A. Verfasser aut Alpha-amino acid derivatives and alpha-fluoro ketones by enantioselective decarboxylation presented by Markus A. Baur 2003 98 Bl. graph. Darst. txt rdacontent n rdamedia nc rdacarrier Regensburg, Univ., Diss., 2003 Ketone (DE-588)4129416-6 gnd rswk-swf Decarboxylierung (DE-588)4148965-2 gnd rswk-swf Fluororganische Verbindungen (DE-588)4154846-2 gnd rswk-swf Asymmetrische Synthese (DE-588)4135603-2 gnd rswk-swf Aminosäurederivate (DE-588)4324626-6 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Fluororganische Verbindungen (DE-588)4154846-2 s Ketone (DE-588)4129416-6 s Asymmetrische Synthese (DE-588)4135603-2 s Decarboxylierung (DE-588)4148965-2 s DE-604 Aminosäurederivate (DE-588)4324626-6 s DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=010481301&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Baur, Markus A. Alpha-amino acid derivatives and alpha-fluoro ketones by enantioselective decarboxylation Ketone (DE-588)4129416-6 gnd Decarboxylierung (DE-588)4148965-2 gnd Fluororganische Verbindungen (DE-588)4154846-2 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd Aminosäurederivate (DE-588)4324626-6 gnd |
| subject_GND | (DE-588)4129416-6 (DE-588)4148965-2 (DE-588)4154846-2 (DE-588)4135603-2 (DE-588)4324626-6 (DE-588)4113937-9 |
| title | Alpha-amino acid derivatives and alpha-fluoro ketones by enantioselective decarboxylation |
| title_auth | Alpha-amino acid derivatives and alpha-fluoro ketones by enantioselective decarboxylation |
| title_exact_search | Alpha-amino acid derivatives and alpha-fluoro ketones by enantioselective decarboxylation |
| title_full | Alpha-amino acid derivatives and alpha-fluoro ketones by enantioselective decarboxylation presented by Markus A. Baur |
| title_fullStr | Alpha-amino acid derivatives and alpha-fluoro ketones by enantioselective decarboxylation presented by Markus A. Baur |
| title_full_unstemmed | Alpha-amino acid derivatives and alpha-fluoro ketones by enantioselective decarboxylation presented by Markus A. Baur |
| title_short | Alpha-amino acid derivatives and alpha-fluoro ketones by enantioselective decarboxylation |
| title_sort | alpha amino acid derivatives and alpha fluoro ketones by enantioselective decarboxylation |
| topic | Ketone (DE-588)4129416-6 gnd Decarboxylierung (DE-588)4148965-2 gnd Fluororganische Verbindungen (DE-588)4154846-2 gnd Asymmetrische Synthese (DE-588)4135603-2 gnd Aminosäurederivate (DE-588)4324626-6 gnd |
| topic_facet | Ketone Decarboxylierung Fluororganische Verbindungen Asymmetrische Synthese Aminosäurederivate Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=010481301&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT baurmarkusa alphaaminoacidderivativesandalphafluoroketonesbyenantioselectivedecarboxylation |