Rhodium-catalyzed hydro-oxycarbonylation of alkynes and allenes: new asymmetric access to branched allylic esters
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Abschlussarbeit Buch |
| Sprache: | English |
| Veröffentlicht: |
München
Verlag Dr. Hut
2015
|
| Ausgabe: | 1. Auflage |
| Schriftenreihe: | Organische Chemie
|
| Schlagworte: | |
| Online-Zugang: | Inhaltstext Inhaltsverzeichnis |
| Beschreibung: | Erscheint auch als Online-Ausgabe: Koschker, Philipp: Rhodium-Catalyzed Hydro-Oxycarbonylation of Alkynes and Allenes: New Asymmetric Access to Branched Allylic Esters |
| Beschreibung: | 6 ungezählte, 315 Seiten Illustrationen, Diagramme 21 cm, 493 g |
| ISBN: | 9783843922463 3843922462 |
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| 245 | 1 | 0 | |a Rhodium-catalyzed hydro-oxycarbonylation of alkynes and allenes |b new asymmetric access to branched allylic esters |c vorgelegt von Philipp Koschker |
| 250 | |a 1. Auflage | ||
| 264 | 1 | |a München |b Verlag Dr. Hut |c 2015 | |
| 300 | |a 6 ungezählte, 315 Seiten |b Illustrationen, Diagramme |c 21 cm, 493 g | ||
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| 490 | 0 | |a Organische Chemie | |
| 500 | |a Erscheint auch als Online-Ausgabe: Koschker, Philipp: Rhodium-Catalyzed Hydro-Oxycarbonylation of Alkynes and Allenes: New Asymmetric Access to Branched Allylic Esters | ||
| 502 | |b Dissertation |c Albert-Ludwigs-Universität Freiburg im Breisgau |d 2015 | ||
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| 653 | |a Allenes | ||
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Datensatz im Suchindex
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TABLE OF CONTENTS
A INTRODUCTION 1
B THEORETICAL BACKGROUND 3
EL SELECTIVITY IN ORGANIC CHEMISTRY 3
B.L.L CHEMOSELECTIVITV 3
B.1.2 REGIOSELECTIVITY 4
B.L
.3 DIASTEREOSELECTIVITY 4
B.L
.4 ENANTIOSELECTIVITY AND ASYMMETRIC CATALYSIS 5
B.L.5 ATOM ECONOMY 6
B.L.6 REDOX ECONOMY AND REDOX NEUTRALITY 7
B.2 ALLYLIC ALCOHOLS AND ALLYLIC ESTERS 8
B.2.1 CLASSIC SYNTHESES 11
B.22 MODEM SYNTHESES BASED ON TRANSITION METAL CATALYSIS 12
B.2.2.1 TRANSITION METAL-CATALYZED ALLYLIC ALKYLATION 13
B.2.2.2 TRANSITION METAL-CATALYZED ALLYLIC OXIDATION IS
BJ ALLYLIC C-H FUNCTIONALIZATION BY ADDITION OF (PRO-)NUCLEOPHILES TO
ALKYNES AND ALLENES
17
B.3.1 ADDITION OF C-NUCLEOPHILES 19
B.3.2 ADDITION OF HET-NUCLEOPHILES 21
B.3.3 ADDITION OF CARBOXYLIC ACIDS TOWARD ALLYLIC ESTERS 24
C TASK 31
D RESULTS AND DISCUSSION 33
D.L ENANTIOSELECTIVE HYDRO-OXYCARBONYLATION OF TERMINAL ALLENES WITH
CARBOXYLIC ACIDS
33
D.L.L REPRODUCIBILITY OF INITIAL RESULTS 33
D.1.2 OPTIMIZATION OF THE REACTION CONDITIONS 35
D.L.3 SUBSTRATE SCOPE 41
D.L
.3.1 SCREENING OF CARBOXYLIC ACID SUBSTRATES 41
D.L.3.2 SCREENING OF TERMINAL ALLENE SUBSTRATES 44
D.1.4 FOLLOW-UP CHEMISTRY AND APPLICATION 49
HTTP://D-NB.INFO/1076051987
TABLE OF CONTENTS
D.1.5 MECHANISTIC INVESTIGATIONS 51
D.1.6 APPLICATION TO INTERNAL ALLENE SUBSTRATES 52
D.2 ENANTIOSELECTIVE HYDRO-OIYCARBONYLATION OF TERMINAL ALKYNES 56
D.2.1 REEVALUATION OF THE RH/(I?,FL)-DIOP (IS) CATALYST SYSTEM 56
D.2.2 OPTIMIZATION OF THE REACTION CONDITIONS WITH (I?,I?)-DIOP (IS) 57
D.2.3 SYNTHESIS AND SCREENING OF DIOP DERIVATIVES 66
D.2.4 SUBSTRATE SCOPE 75
D.2.4.1 SCREENING OF CARBOXYLIC ACID SUBSTRATES 76
D.2.4.2 SCREENING OF TERMINAL ALKYNE SUBSTRATES 79
D.2.5 FOLLOW-UP CHEMISTRY AND APPLICATION 84
D.2.6 MECHANISTIC INVESTIGATIONS 86
E SUMMARY AND OUTLOOK 93
E.1 SUMMARY 93
E.2 OUTLOOK 97
F EXPERIMENTALS 99
F.L GENERAL REMARKS 99
F.L.L CHROMATOGRAPHY 100
F.1.2 NUCLEAR MAGNETIC RESONANCE 101
F.1.3 MASS SPECTROMETRY 101
F.1.4 OPTICAL ROTATION 102
F.1.5 MELTING POINTS 102
F.1.6 DRYING, DEGASSING AND PURIFICATION OF SOLVENTS 102
F.1.7 ORGANOMETALLIC REAGENTS 103
F. 1.8 STARTING MATERIALS AND REAGENTS 104
F.2 LIGAND SYNTHESIS 105
F.2.1 SYNTHESIS OF (FI,^)-DIOP (15) 105
F.2.1.1 (/?,/F)-DIMETHYL 2,3-O-ISOPROPYLIDENTARTRATE (198) 105
F.2.1
-2 (5)-L,4-DIHYDROXY-2,3-0-ISOPROPYLIDENBUTANE(200) 106
F.2.1.3 (5,S)-L,4-DITOSYL-2,3-0-ISOPROPYLIDENBUTANE (199) 107
F.2.1.4 (, DIOP (15) 108
F.2.2 SYNTHESIS OF ( O-ME-DIOP (204) 109
TABLE OF CONTENTS
F.2.3 SYNTHESIS OF (,FL DM-DIOP (205) 110
F.2.3.1 BIS(3,S-DIMETHYLPHENYL)PHOSPHINE OXIDE (202A) 110
F.2.3.2 BIS(3,5-DIMETHYLPHENYL)PHOSPHINE (203A) 111
F .2.3.3 (FT/Y-DM-DLOP (205) 112
F.2.4 SYNTHESIS OF (/^/Y-P-MEO-DIOP (206) 113
F.2.4.1 BIS(4-METHOXYPHENYL)PHOSPHINE(203B) 113
F .2.4.2 (R,R)-P-MEO-DLOP (206) 114
2.5 SYNTHESIS OF (#-DTBM-DIOP (207) 115
F.2.5.1 BIS(3,5-DI-/ERT-BUTYL-4-METHOXYPHENYL)PHOSPHINE (203C) 115
F 2.52 (,R DTBM-D10P (207) 116
F.2.6 SYNTHESIS OF (,/Y-3,5-CF
3
-D10P (208) 117
F.2.7 SYNTHESIS OF (R,RJ-DIOP-DIOL (212) 118
F.2.8 SYNTHESIS OF (^/Y-PH-DIOP (209) 119
F.2.9 SYNTHESIS OF (#-/BU-DIOP (210) 120
F.2.10 SYNTHESIS OF ($-CHEPT-DIOP (211) 121
F.2.11 SYNTHESIS OF (R,TY-CY-D10P (213) 122
F.2.12 SYNTHESIS OF (R,^-CP-DIOP (214) 123
F.2.13 SYNTHESIS OF (K^-CB-DIOP (215) 124
F.2.14 SYNTHESIS OF (R,R 2,3-MEO-DPPB (219) 125
F.2.14.1 (^/?)-DIETHYL 2,3-DIMETHOXYSUCCINATE (217) 125
F.2.14.2 (5
,
4 2,3-DIMETHOXY-L,4-BUTANEDIOL (218) 126
F.2.14.3 (5,5)-1,4-DITOSYL-2,3-DIMETHOXYBUTANE (220) 127
F.2.14.4 (FTTF 2,3-MEO-DPPB (219) 128
FJ2.15 SYNTHESIS OF (R,J-3,6-DPPO (223) 129
F.2.15.1 (5,5J-3,6-DIMESVLOCTANE (222) 129
F.2.15.2 (FT/Y-3,6-DPPO(223) 130
F.3 SUBSTRATE SYNTHESES 131
F.3.1 ALLENE SUBSTRATES 131
F.3.1.1 SYNTHESIS OF OCTA-L,2-DIENE (102D) 131
F.3.1.2 SYNTHESIS OF 1
-PHENYLPROPA-1
,2-DIENE (102E) 132
F.3.1.3 SYNTHESIS OF PENTA-3,4-DIEN-L-YLBENZENE (117A) 133
F.3.1.4 SYNTHESIS OF 5-(TRITYLOXY)PENTA-L ,2-DIENE (102A) 135
F.3.1.5 SYNTHESIS OF 2-(HEXA-4,5-DIEN-L-YL)ISOINDOLINE-L,3-DIONE (102B)
136
F.3.1.6 SYNTHESIS OF L-(PROPA-L,2-DIEN-L-YL)CYCLOHEXANOL (102C) 137
TABLE OF CONTENTS
F.3.1.7 SYNTHESIS OF 3,4,4-TRIMETHYLPENTA-L,2-DIENE (117B) 139
F.3.1.8 SYNTHESIS OF NONA-4,5-DIENE (182A) 141
F.3.1.9 SYNTHESIS OF CYCLONONA-L,2-DIENE (182B) 143
F.3.1.10 SYNTHESIS OF CYCLOTRIDECA-L,2-DIENE (182C) 145
F.3.2 ALKYNE SUBSTRATES 147
F.3.2.1 SYNTHESIS OF 4-WRT-BUTYLDIMETHYLSILOXY 1-BUTYNE (243A) 147
F.3.2.2 SYNTHESIS OF 5-TORT-BUTYIDIMETHYLSILOXY 1-PENTYNE (243B) 148
F.3.2.3 SYNTHESIS OF 6-FERT-BUTYLDIMETHYLSILOXY-L-HEXYNE (243C) 149
F.4 CATALYSIS 150
F.4.1 COUPLING OFCARBOXYLIC ACIDS WITH TERMINAL ALLENES 150
F.4.1.1 GENERAL PROCEDURES 150
F.4.1.2 LIGAND SCREENING 151
F.4.1.3 CONDITION SCREENING 152
F.4.1.4 SYNTHESIS OF THE BRANCHED ALLYLIC ESTER PRODUCTS FIOM ALLENES
153
F.4.1.5 DETERMINATION OF ABSOLUTE CONFIGURATION AND FOLLOW-UP CHEMISTRY
171
F.4.1.6 DEUTERIUM LABELING EXPERIMENTS 174
F.4.2 COUPLING OF CARBOXYLIC ACIDS WITH TERMINAL ALKYNES 178
F.4.2.1 GENERAL PROCEDURES 178
F.4.2.2 CONDITION SCREENING 179
F.4.2.3 LIGAND SCREENING 182
F .4.2.4 SYNTHESIS OF THE BRANCHED ALLYLIC ESTER PRODUCTS FIOM ALKYNES
184
F.4.2.5 FOLLOW-UP CHEMISTRY 205
F.4.2.6 ADDITIONAL INFORMATION FOR THE DFT CALCULATIONS 209
G LIST OF STRUCTURES 211
H APPENDIX 221
I REFERENCES 307 |
| any_adam_object | 1 |
| author | Koschker, Philipp |
| author_GND | (DE-588)1076247288 |
| author_facet | Koschker, Philipp |
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| building | Verbundindex |
| bvnumber | BV043019923 |
| ctrlnum | (OCoLC)934827983 (DE-599)DNB1076051987 |
| dewey-full | 547.215 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547.215 |
| dewey-search | 547.215 |
| dewey-sort | 3547.215 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie |
| edition | 1. Auflage |
| format | Thesis Book |
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| indexdate | 2024-08-03T02:47:03Z |
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| record_format | marc |
| series2 | Organische Chemie |
| spelling | Koschker, Philipp Verfasser (DE-588)1076247288 aut Rhodium-catalyzed hydro-oxycarbonylation of alkynes and allenes new asymmetric access to branched allylic esters vorgelegt von Philipp Koschker 1. Auflage München Verlag Dr. Hut 2015 6 ungezählte, 315 Seiten Illustrationen, Diagramme 21 cm, 493 g txt rdacontent n rdamedia nc rdacarrier Organische Chemie Erscheint auch als Online-Ausgabe: Koschker, Philipp: Rhodium-Catalyzed Hydro-Oxycarbonylation of Alkynes and Allenes: New Asymmetric Access to Branched Allylic Esters Dissertation Albert-Ludwigs-Universität Freiburg im Breisgau 2015 Katalyse (DE-588)4029921-1 gnd rswk-swf Allyl-Stellung (DE-588)4430185-6 gnd rswk-swf Ester (DE-588)4153062-7 gnd rswk-swf Carbonylierung (DE-588)4147316-4 gnd rswk-swf Rhodiumkomplexe (DE-588)4314155-9 gnd rswk-swf Rhodium-Catalyzed Hydro-Oxycarbonylation Alkynes Allenes (DE-588)4113937-9 Hochschulschrift gnd-content Carbonylierung (DE-588)4147316-4 s Katalyse (DE-588)4029921-1 s Rhodiumkomplexe (DE-588)4314155-9 s Ester (DE-588)4153062-7 s Allyl-Stellung (DE-588)4430185-6 s DE-604 Verlag Dr. Hut (München) (DE-588)10174118-2 pbl X:MVB text/html http://deposit.dnb.de/cgi-bin/dokserv?id=f51648b09baf4fefbb11b134ec8983ca&prov=M&dok_var=1&dok_ext=htm Inhaltstext DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=028444769&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Koschker, Philipp Rhodium-catalyzed hydro-oxycarbonylation of alkynes and allenes new asymmetric access to branched allylic esters Katalyse (DE-588)4029921-1 gnd Allyl-Stellung (DE-588)4430185-6 gnd Ester (DE-588)4153062-7 gnd Carbonylierung (DE-588)4147316-4 gnd Rhodiumkomplexe (DE-588)4314155-9 gnd |
| subject_GND | (DE-588)4029921-1 (DE-588)4430185-6 (DE-588)4153062-7 (DE-588)4147316-4 (DE-588)4314155-9 (DE-588)4113937-9 |
| title | Rhodium-catalyzed hydro-oxycarbonylation of alkynes and allenes new asymmetric access to branched allylic esters |
| title_auth | Rhodium-catalyzed hydro-oxycarbonylation of alkynes and allenes new asymmetric access to branched allylic esters |
| title_exact_search | Rhodium-catalyzed hydro-oxycarbonylation of alkynes and allenes new asymmetric access to branched allylic esters |
| title_full | Rhodium-catalyzed hydro-oxycarbonylation of alkynes and allenes new asymmetric access to branched allylic esters vorgelegt von Philipp Koschker |
| title_fullStr | Rhodium-catalyzed hydro-oxycarbonylation of alkynes and allenes new asymmetric access to branched allylic esters vorgelegt von Philipp Koschker |
| title_full_unstemmed | Rhodium-catalyzed hydro-oxycarbonylation of alkynes and allenes new asymmetric access to branched allylic esters vorgelegt von Philipp Koschker |
| title_short | Rhodium-catalyzed hydro-oxycarbonylation of alkynes and allenes |
| title_sort | rhodium catalyzed hydro oxycarbonylation of alkynes and allenes new asymmetric access to branched allylic esters |
| title_sub | new asymmetric access to branched allylic esters |
| topic | Katalyse (DE-588)4029921-1 gnd Allyl-Stellung (DE-588)4430185-6 gnd Ester (DE-588)4153062-7 gnd Carbonylierung (DE-588)4147316-4 gnd Rhodiumkomplexe (DE-588)4314155-9 gnd |
| topic_facet | Katalyse Allyl-Stellung Ester Carbonylierung Rhodiumkomplexe Hochschulschrift |
| url | http://deposit.dnb.de/cgi-bin/dokserv?id=f51648b09baf4fefbb11b134ec8983ca&prov=M&dok_var=1&dok_ext=htm http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=028444769&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT koschkerphilipp rhodiumcatalyzedhydrooxycarbonylationofalkynesandallenesnewasymmetricaccesstobranchedallylicesters AT verlagdrhutmunchen rhodiumcatalyzedhydrooxycarbonylationofalkynesandallenesnewasymmetricaccesstobranchedallylicesters |