Maximizing synthetic efficiency: the development of new multicomponent reactions
Gespeichert in:
| 1. Verfasser: | |
|---|---|
| Format: | Buch |
| Sprache: | English |
| Veröffentlicht: |
2002
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | Rostock, Univ., Diss., 2002 |
| Beschreibung: | II, 222 S.: graph. Darst. 21 cm |
Internformat
MARC
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| 049 | |a DE-29T |a DE-355 | ||
| 100 | 1 | |a Jacobi von Wangelin, Axel |e Verfasser |4 aut | |
| 245 | 1 | 0 | |a Maximizing synthetic efficiency |b the development of new multicomponent reactions |c Axel Jacobi von Wangelin |
| 264 | 1 | |c 2002 | |
| 300 | |a II, 222 S.: graph. Darst. |b 21 cm | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 500 | |a Rostock, Univ., Diss., 2002 | ||
| 650 | 0 | 7 | |a Organische Synthese |0 (DE-588)4075695-6 |2 gnd |9 rswk-swf |
| 650 | 0 | 7 | |a Eintopfreaktion |0 (DE-588)4254931-0 |2 gnd |9 rswk-swf |
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| 689 | 0 | 0 | |a Organische Synthese |0 (DE-588)4075695-6 |D s |
| 689 | 0 | 1 | |a Eintopfreaktion |0 (DE-588)4254931-0 |D s |
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| 943 | 1 | |a oai:aleph.bib-bvb.de:BVB01-010205194 | |
Datensatz im Suchindex
| _version_ | 1807319662860435456 |
|---|---|
| adam_text |
T
ABLE
OF
C
ONTENTS
ABBREVIATIONS
1
1.
INTRODUCTION
1
1.1
E
FFICIENCY
IN
CHEMICAL
SYNTHESIS
1
1.1.1
I
NTRINSIC
EFFICIENCY
1
1.1.2
E
XTRINSIC
EFFICIENCY
'
2
1.1.3
G
REEN
CHEMISTRY
IN
PRACTICE
3
1.1.4
C
OMBINATORIAL
CHEMISTRY
5
14
M
AXIMIZING
EFFICIENCY
WITH
MULTICOMPONENT
REACTIONS
6
1.2.1
M
ULTICOMPONENT
REACTIONS
-
D
EFINITIONS
6
1.2.2
C
OMPLEXITY
AND
DIVERSITY
IN
MULTICOMPONENT
REACTIONS
7
13
H
ISTORICAL
BACKGROUND
OF
MCR
CHEMISTRY
8
1.3.1
C
LASSICS
IN
MCR
CHEMISTRY
8
1.3.2
T
HE
U
GI
REACTION
10
2.
THE
AMIDOCARBONYLATION
OF
ALDEHYDES
_
12
2.1
J
V-ACYLIMINIUM
CHEMISTRY
12
2.1.1
I
NTRODUCTION
12
2.1.2
S
YNTHESIS
AND
REACTIONS
OF
N
ACYLIMINIUM
IONS
13
2.1.3
V-AC
YLIMINIUM
IONS
AND
TRANSITION
METAL
CATALYSIS
14
2.2
THE
TRANSITION
METAL-CATALYZED
AMIDOCARBONYLATION
STATE
OF
THE
ART
15
2.2.1
THE
COBALT-CATALYZED
AMIDOCARBONYLATION
OF
ALDEHYDES
15
2.2.2
T
HE
EMERGENCE
OF
PALLADIUM
CATALYSTS
17
2.2.3
S
COPE
AND
LIMITATIONS
19
23
O
WN
RESULTS
20
2.3.1
DOMINO
REDUCTIVE
CARBONYLATION
-
AMIDOCARBONYLATION
20
2.3.2
S
OLID
-
PHASE
PALLADIUM
-
CATALYZED
AMIDOCARBONYLATION
23
2.3.3
O
PTIMIZATION
OF
THE
PROCEDURE
25
3.
THE
CHEMISTRY
OF
N-ACYL
AMINODIENES
2G
3.1
ALDEHYDE
-
AMIDE
ADDUCTS
28
3.1.1
F
ORMATION
OF
1-W
ACETYLAMINO
-2
METHYL
-1,3
PENTADIENE
28
3.1.2
O
PTIMIZATION
OF
THE
PROCEDURE
29
3.1.3
I
NVESTIGATIONS
INTO
THE
BENZAMIDE
-
BUTYRALDEHYDE
SERIES
32
3.1.4
T
HE
COMPLETE
REACTION
SCHEME
34
34
I-A
CYLAMINO
-1
3
DIENES
-
S
TATE
OF
THE
ART
35
3.2.1
I
NTRODUCTION
35
3.2.2
O
PPOLZER
-O
VERMAN
DIENES
35
3.2.3
O
NE
-
POT
MULTICOMPONENT
APPROACH
37
3.2.4
O
PPOLZER
-O
VERMAN
DIENES
IN
ORGANIC
SYNTHESIS
3
8
33
D
IELS
-A
LDER
REACTIONS
WITH
OUR
I
ACYLAMINO
-13
DIENES
40
3.3.1
3.3.2
3.3.3
R
EACTIONS
WITH
MALEIMIDE
AND
MALEIC
ANHYDRIDE
C
OMPUTATIONAL
RESULTS
R
EACTION
WITH
P
-
BENZOQUINONE
40
40
43
4.
MULTICOMPONENT
REACTIONS
WITH
SIMPLE
ALDEHYDES
_
45
4.1
I
NTRODUCTION
45
4.2
O
NE
-
POT
REACTIONS
WITH
DIENOPHILIC
MALEIMIDE
46
4.2.1
I
NITIAL
STUDIES
OF
A
ONE
-
POT
PROTOCOL
46
4.2.2
L
IBRARY
SYNTHESIS
47
4.2.3
C
HARACTERIZATIONS
50
4.2.4
L
IMITATIONS
52
4.2.5
S
CALE
-
UP
OF
THE
PROCEDURE
53
43
O
NE
-
POT
REACTIONS
WITH
DIENOPHILIC
MALEIC
ANHYDRIDE
53
4.3.1
I
NTRODUCTION
53
4.3.2
L
ITERATURESYNTHESESOF
6
AZABICYCLO
[3.2.1]
OCTANES
54
4.3.3
M
ULTI
-
STEP
VS.
ONE
-
POT
SYNTHESIS
55
4.3.4
L
IBRARY
SYNTHESIS
57
4.3.5
C
HARACTERIZATION
58
4.3.6
AYV-D1METHYLUREA
AS
AMIDE
SOURCE
59
44
ONE-POT
REACTIONS
WITH
DIENOPHILIC
ACRYLONITRILE
60
43
O
NE
-
POT
REACTIONS
WITH
DIENOPHILICP
-
BENZOQUINONE
61
4.5.1
I
NTRODUCTION
61
4.5.2
O
NE
-
POT
PROCEDURE
61
4.5.3
L
ITERATURE
ANALOGS
63
4.5.4
P
ROPOSED
MECHANISM
63
4.5.5
O
PTIMIZATION
OF
THE
PROCEDURE
64
4.6
O
NE
-
POT
REACTION
WITH
DIENOPHILIC
ACETYLENEDICARBOXYLATES
65
4.7
R
EACTIONS
WITH
OTHER
DIENOPHILIC
ALKENES
66
5,
MULTICOMPONENT
REACTIONS
WITH
UNSATURATED
CARBONYL
COMPOUNDS
68
5.1
I
NTRODUCTION
68
5
J
O
NE
-
POT
REACTIONS
WITH
DIENOPHILIC
MALEIMIDES
69
5.2.1
L
IBRARY
SYNTHESIS
69
5.2.2
C
HARACTERIZATION
72
5.2.3
S
ULFUR
-
CONTAINING
MCR
ADDUCTS
72
5.2.4
H
ALOARENE
-
BEARING
COMPOUNDS
74
5.2.5
R
EACTIONS
WITH
SECONDARY
AMIDES
75
5.2.6
D
IMERIC
ARCHITECTURES
76
53
ONE-POT
REACTIONS
WITH
,P-UNSATURATED
KETONES
77
5.3.1
I
NTRODUCTION
77
5.3.2
M
ODEL
REACTION
78
54
ONE-POT
REACTIONS
WITH
DIENOPHILIC
MALEIC
ANHYDRIDE
79
53
ONE-POT
REACTIONS
WITH
DIENOPHILIC
ACRYLONITRILE
80
5.5.1
I
NITIAL
RESULTS
80
5.5.2
O
PTIMIZATION
OF
THE
PROCEDURE
81
5.5.3
S
YNTHESIS
OF
RELATED
ADDUCTS
82
5.6
ONE-POT
REACTIONS
WITH
DIENOPHILIC
ACETYLENEDICARBOXYLATES
84
5.6.1
R
EACTIONS
WITH
SUBSTITUTED
2
PENTENALS
AND
HIGHER
HOMOLOGS
84
5.6.2
R
EACTIONS
WITH
SUBSTITUTED
CROTONALDEHYDES
85
6.
ENANTIOSELECTIVE
VARIANTS
_
96
6.1
C
HIRAL
DIENOPHILES
96
6.2
CHIRAL
CARBOXAMIDES
99
63
L
EWIS
ACID
CATALYSTS
100
64
E
NZYMATIC
KINETIC
RESOLUTION
OF
D
IELS
-
ALDER
ADDUCTS
102
7,
POST-MCR
MODIFICATIONS
_
103
7.1
I
NTRODUCTION
103
7.2
S
UBSTITUTED
ANILIDES
105
7.2.1
O
XIDATION
WITH
MNO
2
105
7.2.2
O
NE
-
POT
PROCEDURES
106
73
R
EPEATED
D
IELS
-A
LDER
REACTION
WITH
ACYLAMINODIENES
107
73.1
D
OMINO
ELIMINATION
-D
IELS
-
ALDER
REACTIONS
107
73.2
O
NE
-
POT
PROCEDURE
109
7.3.3
A
MIDE
CATALYSIS
110
74
I
NTRAMOLECULAR
H
ECK
REACTIONS
111
7.4.1
I
NTRODUCTION
111
7.4.2
P
HENANTHRIDONES
112
7.4.3
H
ECK
CHEMISTRY
WITH
MALEIMIDE
-
BEARING
MCR
ADDUCTS
113
7.4.4
S
ECOND
GENERATION
APPROACH
WITH
NITRILES
116
7.5
P
HOTO
COCYCLIZATION
WITH
ALKYNES
118
7.5.1
I
NTRODUCTION
118
7.5.2
I
NITIAL
RESULTS
119
8,
SUMMARY
121
9.
EXPERIMENTAL
SECTION
_128
9.1
G
ENERAL
128
9.1.1
R
EAGENTS
128
9.1.2
A
NALYTICS
128
9.1.3
R
EACTION
EQUIPMENT
129
9.2
P
ALLADIUM
-
CATALYZED
CARBONYLATION
AND
AMIDOCARBONYLATION
130
9.2.1
P
ALLADIUM
-
CATALYZED
REDUCTIVE
CARBONYLATION
OF
BROMOARENES
130
9.2.2
P
ALLADIUM
-
CATALYZED
AMIDOCARBONYLATION
OF
BENZALDEHYDES
130
9.2.3
S
OLID
-
PHASE
AMIDOCARBONYLATION
OFP
-
HYDROXYBENZALDEHYDE
131
93
A
MIDE
-
ALDEHYDE
ADDUCTS
133
9.4
D
IELS
-
ALDER
REACTIONS
WITH
AMINODIENE
101
136
9.5
M
ULTICOMPONENT
COUPLING
WITH
SIMPLE
ALDEHYDES
138
9.5.1
R
EACTIONS
WITH
DIENOPHILIC
MALEIMIDES
139
9.5.2
R
EACTIONS
WITH
DIENOPHILIC
MALEIC
ANHYDRIDE
146
9.5.3
R
EACTIONS
WITH
DIENOPHILIC
ACRYLONITRILE
151
9.5.4
R
EACTIONS
WITH
DIENOPHILICP
-
BENZOQUINONE
152
9.5.5
R
EACTIONS
WITH
DIENOPHILIC
DIETHYL
ACETYLENEDICARBOXYLATE
153
9.5.6
R
EACTIONS
WITH
OTHER
DIENOPHILES
156
9.6
M
ULTICOMPONENT
REACTIONS
WITH
X
,|J
UNSATURATED
CARBONYL
COMPOUNDS
158
9.6.1
R
EACTIONS
WITH
DIENOPHILIC
MALEIMIDES
158
9.6.2
R
EACTION
WITH
AN
A,
P
UNSATURATED
KETONE
AND
DIENOPHILIC
MALEIMIDE
174
9.6.3
R
EACTIONS
WITH
DIENOPHILIC
MALEIC
ANHYDRIDE
175
9.6.4
R
EACTIONS
WITH
DIENOPHILIC
ACRYLONITRILE
176
9.6.5
R
EACTIONS
WITH
DIENOPHILIC
ETHYL
ACETYLENECARBOXYLATES
181
9.7
S
TEREOSELECTIVE
VERSIONS
189
9.7.1
C
HIRAL
DIENOPHILES
189
9.7.2
C
HIRAL
CARBOXAMIDES
192
9.7.3
C
HIRAL
TRANSITION
-
METAL
CATALYSIS
192
94)
P
OST
-
SYNTHESIS
MODIFICATIONS
193
9.8.1
A
NILINES
VIA
M
II
O
I
-
MEDIATED
OXIDATION
193
9.8.2
T
ETRACYCLIC
DOUBLE
D
IELS
-A
LDER
ADDUCTS
195
9.8.3
I
NTRAMOLECULAR
H
ECK
REACTIONS
197
9.8.5
C
OCYCLIZATION
OF
ETHYNE
WITH
NITRILES
200
9.9
C
RYSTALLOGRAPHIC
DATA
AND
REFINEMENT
201
9.10
C
OMPUTATIONAL
CALCULATIONS
206
10,
REFERENCES
_
207 |
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| genre | (DE-588)4113937-9 Hochschulschrift gnd-content |
| genre_facet | Hochschulschrift |
| id | DE-604.BV016510735 |
| illustrated | Not Illustrated |
| indexdate | 2024-08-14T00:12:23Z |
| institution | BVB |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-010205194 |
| oclc_num | 248946323 |
| open_access_boolean | |
| owner | DE-29T DE-355 DE-BY-UBR |
| owner_facet | DE-29T DE-355 DE-BY-UBR |
| physical | II, 222 S.: graph. Darst. 21 cm |
| publishDate | 2002 |
| publishDateSearch | 2002 |
| publishDateSort | 2002 |
| record_format | marc |
| spelling | Jacobi von Wangelin, Axel Verfasser aut Maximizing synthetic efficiency the development of new multicomponent reactions Axel Jacobi von Wangelin 2002 II, 222 S.: graph. Darst. 21 cm txt rdacontent n rdamedia nc rdacarrier Rostock, Univ., Diss., 2002 Organische Synthese (DE-588)4075695-6 gnd rswk-swf Eintopfreaktion (DE-588)4254931-0 gnd rswk-swf (DE-588)4113937-9 Hochschulschrift gnd-content Organische Synthese (DE-588)4075695-6 s Eintopfreaktion (DE-588)4254931-0 s DE-604 DNB Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=010205194&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Jacobi von Wangelin, Axel Maximizing synthetic efficiency the development of new multicomponent reactions Organische Synthese (DE-588)4075695-6 gnd Eintopfreaktion (DE-588)4254931-0 gnd |
| subject_GND | (DE-588)4075695-6 (DE-588)4254931-0 (DE-588)4113937-9 |
| title | Maximizing synthetic efficiency the development of new multicomponent reactions |
| title_auth | Maximizing synthetic efficiency the development of new multicomponent reactions |
| title_exact_search | Maximizing synthetic efficiency the development of new multicomponent reactions |
| title_full | Maximizing synthetic efficiency the development of new multicomponent reactions Axel Jacobi von Wangelin |
| title_fullStr | Maximizing synthetic efficiency the development of new multicomponent reactions Axel Jacobi von Wangelin |
| title_full_unstemmed | Maximizing synthetic efficiency the development of new multicomponent reactions Axel Jacobi von Wangelin |
| title_short | Maximizing synthetic efficiency |
| title_sort | maximizing synthetic efficiency the development of new multicomponent reactions |
| title_sub | the development of new multicomponent reactions |
| topic | Organische Synthese (DE-588)4075695-6 gnd Eintopfreaktion (DE-588)4254931-0 gnd |
| topic_facet | Organische Synthese Eintopfreaktion Hochschulschrift |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=010205194&sequence=000001&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
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