Modern organocopper chemistry:
Gespeichert in:
| Format: | Buch |
|---|---|
| Sprache: | English |
| Veröffentlicht: |
Weinheim
Wiley-VCH
2002
|
| Schlagworte: | |
| Online-Zugang: | Inhaltsverzeichnis |
| Beschreibung: | XIV, 377 S. Ill., graph. Darst. |
| ISBN: | 3527297731 |
Internformat
MARC
| LEADER | 00000nam a22000008c 4500 | ||
|---|---|---|---|
| 001 | BV014111835 | ||
| 003 | DE-604 | ||
| 005 | 20021211 | ||
| 007 | t | ||
| 008 | 020122s2002 gw ad|| |||| 00||| eng d | ||
| 016 | 7 | |a 963560336 |2 DE-101 | |
| 020 | |a 3527297731 |9 3-527-29773-1 | ||
| 035 | |a (OCoLC)47676544 | ||
| 035 | |a (DE-599)BVBBV014111835 | ||
| 040 | |a DE-604 |b ger |e rakddb | ||
| 041 | 0 | |a eng | |
| 044 | |a gw |c DE | ||
| 049 | |a DE-29T |a DE-703 |a DE-355 |a DE-91G |a DE-19 |a DE-20 |a DE-11 |a DE-188 | ||
| 050 | 0 | |a QD412.C9 | |
| 082 | 0 | |a 547/.05652 |2 21 | |
| 084 | |a VK 7783 |0 (DE-625)147509: |2 rvk | ||
| 084 | |a CHE 330f |2 stub | ||
| 084 | |a CHE 622f |2 stub | ||
| 245 | 1 | 0 | |a Modern organocopper chemistry |c ed. by Norbert Krause |
| 264 | 1 | |a Weinheim |b Wiley-VCH |c 2002 | |
| 300 | |a XIV, 377 S. |b Ill., graph. Darst. | ||
| 336 | |b txt |2 rdacontent | ||
| 337 | |b n |2 rdamedia | ||
| 338 | |b nc |2 rdacarrier | ||
| 650 | 4 | |a Composés organocuivreux - Guides, manuels, etc | |
| 650 | 4 | |a Organocopper compounds | |
| 650 | 0 | 7 | |a Kupferorganische Verbindungen |0 (DE-588)4166139-4 |2 gnd |9 rswk-swf |
| 655 | 7 | |0 (DE-588)4143413-4 |a Aufsatzsammlung |2 gnd-content | |
| 689 | 0 | 0 | |a Kupferorganische Verbindungen |0 (DE-588)4166139-4 |D s |
| 689 | 0 | |5 DE-604 | |
| 700 | 1 | |a Krause, Norbert |e Sonstige |4 oth | |
| 856 | 4 | 2 | |m HBZ Datenaustausch |q application/pdf |u http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009668775&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |3 Inhaltsverzeichnis |
| 999 | |a oai:aleph.bib-bvb.de:BVB01-009668775 | ||
Datensatz im Suchindex
| _version_ | 1804128980329037824 |
|---|---|
| adam_text | Contents
Foreword v
Preface xi
List of Authors xiii
1 Structures and Reactivities of Organocopper Compounds 1
Johann T. B. H. Jastrzebski, Gerard van Koten
1.1 Introduction 1
1.1.1 Historical Perspective 1
1.1.2 The Oxidation States of Copper 3
1.1.3 Thermal Stability and Bonding in Organocopper(I) Compounds 6
1.2 Homoleptic Organocopper Compounds CunRn 8
1.3 Heteroleptic Organocopper Compounds Cun+mRnXm 17
1.4 Organocuprates 26
1.4.1 Neutral Homoleptic and Heteroleptic Organocuprates 27
1.4.2 Anionic Homoleptic and Heteroleptic Organocuprates 32
1.4.3 Lower- and Higher-order Cyanocuprates 34
1.5 Concluding Remarks 37
Acknowledgement 40
References 40
2 Transmetalation Reactions Producing Organocopper Reagents 45
Paul Knochel, Bodo Betzemeier
2.1 Introduction 45
2.2 Transmetalation of Functionalized Organolithium and Organomagnesium
Reagents 45
2.3 Transmetalation of Organoboron and Organoaluminium Reagents 51
2.4 Transmetalation of Functionalized Organozinc Reagents 54
2A.I Preparation of Organozinc Reagents 54
2.4.1.1 Preparation of Organozinc Halides 56
2.4.1.2 Preparation of Diorganozinc Reagents 59
2.4.2 Substitution Reactions with Copper-Zinc Reagents 62
2.4.3 Addition Reactions with Copper-Zinc Reagents 65
2.5 Transmetalation of Organotin, Organosulfur, and Organotellurium
Reagents 67
2.6 Transmetalation of Organotitanium and Organomanganese Reagents 70
2.7 Transmetalation of Organozirconium and Organosamanum Reagents 71
2.8 Conclusion 74
References 75
3 Heteroatomcuprates and a-Heteroatomalkylcuprates in Organic Synthesis 79
R. Karl Dieter
3.1 Introduction 79
3.2 Heteroatomcuprates 80
3.2.1 Group IVA Heteroatoms (Si, Ge, Sn) 80
3.2.1.1 Conjugate Addition Reactions 83
3.2.1.2 Silylcupration and Stannylcupration of Alkynes and Allenes 93
3.2.1.3 Substitution Reactions 102
3.2.2 Group VA and VIA Heteroatoms (N, O, P) 108
3.3 a-Heteroatomalkylcuprates 109
3.3.1 Group VI Heteroatoms (O, S, Se) 110
3.3.2 Group V Heteroatoms (N, P) and Silicon 114
3.3.3 a-Fluoroalkylcuprates and a-Fluoroalkenylcuprates 122
3.4 Non-transferable Heteroatom(alkyl)cuprates and a-
Heteroatomalkylcuprates 123
3.4.1 Simple Residual Ligands 124
3.4.2 Crural Ligands 127
3.5 Summary 133
Acknowledgments 134
References 134
4 Copper-mediated Addition and Substitution Reactions of Extended Multiple
Bond Systems 145
Norbert Krause, Anja Hoffmann-Roder
4.1 Introduction 145
4.2 Copper-mediated Addition Reactions to Extended Michael Acceptors 146
4.2.1 Acceptor-substituted Dienes 146
4.2.2 Acceptor-substituted Enynes 150
4.2.3 Acceptor-substituted Polyenynes 159
4.3 Copper-mediated Substitution Reactions of Extended Substrates 160
4.4 Conclusion 162
References 163
5 Copper(l)-mediated 1,2- and 1,4-Reductions 167
Bruce H. Lipshutz
5.1 Introduction and Background 167
5.2 More Recent Developments: Stoichiometric Copper Hydride Reagents 168
5.3 1,4-Reductions Catalytic in Cu(I) 174
5.4 1,2-Reductions Catalyzed by Copper Hydride 179
5.5 Heterogeneous CuH-Catalyzed Reductions 182
5.6 Overview and Future Developments 184
References 385
I
6 Copper-mediated Diastereoselective Conjugate Addition and Allylic Substitution
Reactions 188
Bernhard Breit, Peter Demel
Abstract 188
6.1 Conjugate Addition 188
6.1.1 Stereocontrol in Cyclic Derivatives 188
6.1.2 Stereocontrol in Acyclic Derivatives 192
6.1.2.1 y-Heteroatom-substituted Michael Acceptors 192
6.1.2.2 y-Alkyl-substituted a,/?-Unsaturated Carbonyl Derivatives 198
6.1.2.3 a,/?-Unsaturated Carbonyl Derivatives with Stereogenic Centers in
Positions other than the y-Position 200
6.1.2.4 Directed Conjugate Addition Reactions 200
6.1.3 Auxiliary-bound Chiral Michael Acceptors and Auxiliary Chiral Metal
Complexes 202
6.2 Allylic Substitution 210
References 218
7 Copper-catalyzed Enantioselective Conjugate Addition Reactions of Organozinc
Reagents 224
Ben L. Feringa, Robert Naasz, Rosalmde Imbos, Leggy A. Arnold
7.1 Introduction 224
7.2 Organozinc Reagents 227
7.3 Copper-catalyzed 1,4-Addition 229
7.3.1 Phosphoramidite-based Catalysts 229
7.3.2 Catalytic Cycle 233
7.3.3 Variation of Ligands 234
7.3.4 Cyclic Enones 239
7.3.5 2-Cyclopentenone 240
7.3.6 Acyclic Enones 242
7.4 Synthetic Applications 243
7 A.I Tandem Conjugate Addition-Aldol Reactions 243
7.4.2 Kinetic Resolution of 2-Cyclohexenones 243
7A3 Sequential 1,4-Additions to 2,5-Cyclohexadienones 246
7.4.4 Lactones 250
7.4.5 Nitroalkenes 250
7.4.6 Annulation Methodology 252
7.5 Conclusions 254
Acknowledgements 255
References and Notes 255
8 Copper-Mediated Enantioselective Substitution Reactions 259
A. Sofia E. Karlstrom, Jan-Erling Backvall
8.1 Introduction 259
8.2 Allylic Substitution 261
8.2.1 Allylic Substrates with Chiral Leaving Groups 262
8.2.2 Chiral Auxiliary that is Cleaved off after the Reaction 268
8.2.3 Catalytic Reactions with Chiral Ligands 272
8.3 Epoxides and Related Substrates 283
8.4 Concluding Remarks 286
References and Notes 286
9 Copper-Mediated Synthesis of Natural and Unnatural Products 289
Yukiyasu Chounan, Yoshinori Yamamoto
Abstract 289
9.1 Conjugate Addition 289
9.2 SN2 Substitution 296
9.3 SN2 Substitution 302
9.4 1,2-Metalate Rearrangements 306
9.5 Carbocupration 309
References 310
10 Mechanisms of Copper-mediated Addition and Substitution Reactions 315
Seiji Mori, Eiichi Nakamura
10.1 Introduction 325
10.2 Conjugate Addition Reaction 318
10.2.1 Four-centered and Six-centered Mechanisms 318
10.2.2 Single-electron Transfer Theorem 319
10.2.3 Kinetic and Spectroscopic Analysis of Intermediates 320
10.2.4 Catalytic Conjugate Addition 322
10.2.5 Theoretically Based Conjugate Addition Reaction Pathway 322
10.3 Carbocupration Reactions of Acetylenes and Olefins 324
10.3.1 Experimental Facts 324
10.3.2 Theoretically Based Carbocupration Reaction Pathway 325
10.4 Substitution Reactions on Carbon Atoms 327
10.4.1 SN2 Mechanism of Stoichiometric Substitution Reactions 327
10.4.2 SN2 Allylation Reactions 329
10.4.3 Radical Substitution Reaction Mechanisms 330
10.4.4 Catalytic Substitution Reactions 330
10.4.5 Theoretically Based Alkylation Reaction Pathways 330
10.6 Other Issues 332
10.6.1 Counter-cation Lewis Acid Effects 332
10.6.2 Me3SiCl Acceleration 333
10.6.3 Dummy Ligands 335
10.6.4 The Higher Order Cuprate Controversy 337
10.6.5 Further Issues 338
10.7 Orbital Interactions in Copper-mediated Reactions 338
10.8 The Roles of Cluster Structure in Copper-mediated Reactions 339
10.9 Summary and Outlook 340
References 340
Author Index 347
Subject Index 369
|
| any_adam_object | 1 |
| building | Verbundindex |
| bvnumber | BV014111835 |
| callnumber-first | Q - Science |
| callnumber-label | QD412 |
| callnumber-raw | QD412.C9 |
| callnumber-search | QD412.C9 |
| callnumber-sort | QD 3412 C9 |
| callnumber-subject | QD - Chemistry |
| classification_rvk | VK 7783 |
| classification_tum | CHE 330f CHE 622f |
| ctrlnum | (OCoLC)47676544 (DE-599)BVBBV014111835 |
| dewey-full | 547/.05652 |
| dewey-hundreds | 500 - Natural sciences and mathematics |
| dewey-ones | 547 - Organic chemistry |
| dewey-raw | 547/.05652 |
| dewey-search | 547/.05652 |
| dewey-sort | 3547 45652 |
| dewey-tens | 540 - Chemistry and allied sciences |
| discipline | Chemie / Pharmazie Chemie |
| format | Book |
| fullrecord | <?xml version="1.0" encoding="UTF-8"?><collection xmlns="http://www.loc.gov/MARC21/slim"><record><leader>01565nam a22004218c 4500</leader><controlfield tag="001">BV014111835</controlfield><controlfield tag="003">DE-604</controlfield><controlfield tag="005">20021211 </controlfield><controlfield tag="007">t</controlfield><controlfield tag="008">020122s2002 gw ad|| |||| 00||| eng d</controlfield><datafield tag="016" ind1="7" ind2=" "><subfield code="a">963560336</subfield><subfield code="2">DE-101</subfield></datafield><datafield tag="020" ind1=" " ind2=" "><subfield code="a">3527297731</subfield><subfield code="9">3-527-29773-1</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(OCoLC)47676544</subfield></datafield><datafield tag="035" ind1=" " ind2=" "><subfield code="a">(DE-599)BVBBV014111835</subfield></datafield><datafield tag="040" ind1=" " ind2=" "><subfield code="a">DE-604</subfield><subfield code="b">ger</subfield><subfield code="e">rakddb</subfield></datafield><datafield tag="041" ind1="0" ind2=" "><subfield code="a">eng</subfield></datafield><datafield tag="044" ind1=" " ind2=" "><subfield code="a">gw</subfield><subfield code="c">DE</subfield></datafield><datafield tag="049" ind1=" " ind2=" "><subfield code="a">DE-29T</subfield><subfield code="a">DE-703</subfield><subfield code="a">DE-355</subfield><subfield code="a">DE-91G</subfield><subfield code="a">DE-19</subfield><subfield code="a">DE-20</subfield><subfield code="a">DE-11</subfield><subfield code="a">DE-188</subfield></datafield><datafield tag="050" ind1=" " ind2="0"><subfield code="a">QD412.C9</subfield></datafield><datafield tag="082" ind1="0" ind2=" "><subfield code="a">547/.05652</subfield><subfield code="2">21</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">VK 7783</subfield><subfield code="0">(DE-625)147509:</subfield><subfield code="2">rvk</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">CHE 330f</subfield><subfield code="2">stub</subfield></datafield><datafield tag="084" ind1=" " ind2=" "><subfield code="a">CHE 622f</subfield><subfield code="2">stub</subfield></datafield><datafield tag="245" ind1="1" ind2="0"><subfield code="a">Modern organocopper chemistry</subfield><subfield code="c">ed. by Norbert Krause</subfield></datafield><datafield tag="264" ind1=" " ind2="1"><subfield code="a">Weinheim</subfield><subfield code="b">Wiley-VCH</subfield><subfield code="c">2002</subfield></datafield><datafield tag="300" ind1=" " ind2=" "><subfield code="a">XIV, 377 S.</subfield><subfield code="b">Ill., graph. Darst.</subfield></datafield><datafield tag="336" ind1=" " ind2=" "><subfield code="b">txt</subfield><subfield code="2">rdacontent</subfield></datafield><datafield tag="337" ind1=" " ind2=" "><subfield code="b">n</subfield><subfield code="2">rdamedia</subfield></datafield><datafield tag="338" ind1=" " ind2=" "><subfield code="b">nc</subfield><subfield code="2">rdacarrier</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Composés organocuivreux - Guides, manuels, etc</subfield></datafield><datafield tag="650" ind1=" " ind2="4"><subfield code="a">Organocopper compounds</subfield></datafield><datafield tag="650" ind1="0" ind2="7"><subfield code="a">Kupferorganische Verbindungen</subfield><subfield code="0">(DE-588)4166139-4</subfield><subfield code="2">gnd</subfield><subfield code="9">rswk-swf</subfield></datafield><datafield tag="655" ind1=" " ind2="7"><subfield code="0">(DE-588)4143413-4</subfield><subfield code="a">Aufsatzsammlung</subfield><subfield code="2">gnd-content</subfield></datafield><datafield tag="689" ind1="0" ind2="0"><subfield code="a">Kupferorganische Verbindungen</subfield><subfield code="0">(DE-588)4166139-4</subfield><subfield code="D">s</subfield></datafield><datafield tag="689" ind1="0" ind2=" "><subfield code="5">DE-604</subfield></datafield><datafield tag="700" ind1="1" ind2=" "><subfield code="a">Krause, Norbert</subfield><subfield code="e">Sonstige</subfield><subfield code="4">oth</subfield></datafield><datafield tag="856" ind1="4" ind2="2"><subfield code="m">HBZ Datenaustausch</subfield><subfield code="q">application/pdf</subfield><subfield code="u">http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009668775&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA</subfield><subfield code="3">Inhaltsverzeichnis</subfield></datafield><datafield tag="999" ind1=" " ind2=" "><subfield code="a">oai:aleph.bib-bvb.de:BVB01-009668775</subfield></datafield></record></collection> |
| genre | (DE-588)4143413-4 Aufsatzsammlung gnd-content |
| genre_facet | Aufsatzsammlung |
| id | DE-604.BV014111835 |
| illustrated | Illustrated |
| indexdate | 2024-07-09T18:57:51Z |
| institution | BVB |
| isbn | 3527297731 |
| language | English |
| oai_aleph_id | oai:aleph.bib-bvb.de:BVB01-009668775 |
| oclc_num | 47676544 |
| open_access_boolean | |
| owner | DE-29T DE-703 DE-355 DE-BY-UBR DE-91G DE-BY-TUM DE-19 DE-BY-UBM DE-20 DE-11 DE-188 |
| owner_facet | DE-29T DE-703 DE-355 DE-BY-UBR DE-91G DE-BY-TUM DE-19 DE-BY-UBM DE-20 DE-11 DE-188 |
| physical | XIV, 377 S. Ill., graph. Darst. |
| publishDate | 2002 |
| publishDateSearch | 2002 |
| publishDateSort | 2002 |
| publisher | Wiley-VCH |
| record_format | marc |
| spelling | Modern organocopper chemistry ed. by Norbert Krause Weinheim Wiley-VCH 2002 XIV, 377 S. Ill., graph. Darst. txt rdacontent n rdamedia nc rdacarrier Composés organocuivreux - Guides, manuels, etc Organocopper compounds Kupferorganische Verbindungen (DE-588)4166139-4 gnd rswk-swf (DE-588)4143413-4 Aufsatzsammlung gnd-content Kupferorganische Verbindungen (DE-588)4166139-4 s DE-604 Krause, Norbert Sonstige oth HBZ Datenaustausch application/pdf http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009668775&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA Inhaltsverzeichnis |
| spellingShingle | Modern organocopper chemistry Composés organocuivreux - Guides, manuels, etc Organocopper compounds Kupferorganische Verbindungen (DE-588)4166139-4 gnd |
| subject_GND | (DE-588)4166139-4 (DE-588)4143413-4 |
| title | Modern organocopper chemistry |
| title_auth | Modern organocopper chemistry |
| title_exact_search | Modern organocopper chemistry |
| title_full | Modern organocopper chemistry ed. by Norbert Krause |
| title_fullStr | Modern organocopper chemistry ed. by Norbert Krause |
| title_full_unstemmed | Modern organocopper chemistry ed. by Norbert Krause |
| title_short | Modern organocopper chemistry |
| title_sort | modern organocopper chemistry |
| topic | Composés organocuivreux - Guides, manuels, etc Organocopper compounds Kupferorganische Verbindungen (DE-588)4166139-4 gnd |
| topic_facet | Composés organocuivreux - Guides, manuels, etc Organocopper compounds Kupferorganische Verbindungen Aufsatzsammlung |
| url | http://bvbr.bib-bvb.de:8991/F?func=service&doc_library=BVB01&local_base=BVB01&doc_number=009668775&sequence=000002&line_number=0001&func_code=DB_RECORDS&service_type=MEDIA |
| work_keys_str_mv | AT krausenorbert modernorganocopperchemistry |