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[资源] A Green Chemistry Approach to Asymmetric Catalysis（Chem Review）

A Green Chemistry Approach to Asymmetric Catalysis: Solvent-Free and Highly Concentrated Reactions
Patrick J. Walsh,*,† Hongmei Li,† and Cecilia Anaya de Parrodi*,‡
P. Roy and Diana T. Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, 231 South 34th Street, Philadelphia,
Pennsylvania 19104-6323, and Departamento de Ciencias Quı´mico Biolo´gicas, Universidad de las Ame´ricas-Puebla, Santa Catarina Ma´rtir s/n,
Cholula Puebla, 72820, Me´xico

Contents
1. Introduction and Scope 1
2. Solvent-Free and Highly Concentrated Reactions in Asymmetric Catalysis
2.1. Epoxide-Opening Reactions 3
2.1.1. Desymmetrization of meso-Epoxides 3
2.1.2. Mechanistic Investigations and Implications for Solvent-Free Epoxide Opening
2.1.3. ARO of meso-Epoxides with Benzoic Acid 5
2.2. Reactions with Racemic Epoxides 5
2.2.1. Kinetic Resolution of Epoxides with Me3SiN3  5
2.2.2. Dynamic Kinetic Resolution of Epichlorohydrin 6
2.2.3. Hydrolytic Kinetic Resolution of Epoxides 7
2.2.4. Oligomeric (salen)Co(III) Catalysts for the HKR  8
2.2.5. Supported (salen)Co(III) Catalyst for the HKR  11
2.2.6. Asymmetric Ring Opening of Epoxides Using Carbon Dioxide 11
2.3. Asymmetric Hetero-Diels-Alder Reaction 12
2.3.1. Asymmetric Hetero-Diels-Alder Reaction of Danishefsky’s Diene and Aldehydes 13
2.3.2. Hetero-Diels-Alder Reaction Catalyzed by (salen)Cr(X) Complexes 14
2.3.3. Organocatalytic Hetero-Diels-Alder Reaction Catalyzed by TADDOLDerivatives 15
2.3.4. Diastereoselective Hetero-Diels-Alder Reaction 15
2.3.5. Asymmetric Hetero-Diels-Alder Reaction of Danishefsky’s Diene with N-Aryl Imines 16
2.3.6. Asymmetric Hetero-Diels-Alder Reaction of Brassard’s Diene and Aldehydes  17
2.3.7. Asymmetric Hetero-Diels-Alder Reaction of Mono-oxygenated Dienes and Aldehydes 17
2.4. Asymmetric Metathesis Reactions 19
2.4.1. Asymmetric Ring-Closing Metathesis Reactions 19
2.4.2. Asymmetric Ring-Opening Metathesis/ Cross-Metathesis Reactions 20
2.5. Asymmetric Carbonyl-Ene Reaction 20
2.5.1. Self-Supported (BINOLate)Ti-Based Catalysts for the Carbonyl-Ene Reaction 21
2.6. Asymmetric Addition of Organometallic Reagents to Aldehydes and Ketones 21
2.6.1. Enantioselective Alkylation of Aldehydes with Dialkylzinc Reagents 21
2.6.2. Catalytic Asymmetric Acetylide Additions to Aldehydes 23
2.6.3. Asymmetric Addition of Alkyl Groups to Ketones 23
2.6.4. Asymmetric Allylation of Ketones 27
2.7. Lewis Acid Catalyzed Asymmetric Michael Reactions 29
2.8. Asymmetric Friedel-Crafts with Aromatic Ethers 29
2.9. Asymmetric Pauson-Khand-Type Reaction 30
2.10. Asymmetric Hydroformylation 31
2.10.1. Heterogeneous Asymmetric Hydroformylation Reactions 32
2.11. Asymmetric Hydrogenation Reaction 33
2.12. Asymmetric Hydrosilylation of Ketones 34
2.13. Asymmetric Allylic Amination 35
2.14. Asymmetric Conjugate Addition of Cyanide to R,â-Unsaturated Imides 35
2.15. Asymmetric Organocatalytic Reactions 36
2.15.1. Asymmetric Hajos-Parrish Reaction 36
2.15.2. Enantioselective Aldol Reaction 37
2.15.3. Enantioselective Morita-Baylis-Hillman Reaction 37
2.15.4. Enantioselective Organocatalytic Conjugate Additions 38
2.15.5. R-Amination of Ketones 39
3. Outlook 39
4. Abbreviations 39
5. Acknowledgments 40
6. References 40
1. Introduction and Scope
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http://emuch.net/html/200605/240146.html(转）

ISI 推荐的近10年(1995-2005)在Asymmetric Catalysis方面最具影响力的20篇文献，您知道吗？

***Article 1
Total Cites: 980
Article Title: Asymmetric transition metal-catalyzed allylic alkylations
Authors: Trost, BM, Vanvranken, DL
Journal: CHEMICAL REVIEWS
Volume: 96
Page: 395-422
Year: 1996
Addresses:
· UNIV CALIF IRVINE, DEPT CHEM, IRVINE, CA, USA

***Article 2
Total Cites: 484
Article Title: Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes
Authors: Noyori, R, Hashiguchi, S
Journal: ACCOUNTS CHEM RES
Volume: 30
Page: 97-102
Year: 1997
Addresses:

***Article 3
Total Cites: 421
Article Title: C-2-symmetric chiral bis(oxazoline)-metal complexes in catalytic asymmetric synthesis
Authors: Ghosh, AK, Packiarajan, M, Cappiello, J
Journal: TETRAHEDRON-ASYMMETR
Volume: 9
Page: 1
Year: 1998
Addresses:
· Univ Illinois, Dept Chem, Chicago, IL, USA

***Article 4
Total Cites: 398
Article Title: 1,1 '-binaphthyl dimers, oligomers, and polymers: Molecular recognition, asymmetric catalysis, and new materials
Authors: Pu, L
Journal: CHEMICAL REVIEWS
Volume: 98
Page: 2405-2494
Year: 1998
Addresses:
· Univ Virginia, Dept Chem, Charlottesville, VA, USA

***Article 5
Total Cites: 373
Article Title: Asymmetric catalysis with water: Efficient kinetic resolution of terminal epoxides by means of catalytic hydrolysis
Authors: Tokunaga, M, Larrow, JF, Kakiuchi, F, Jacobsen, EN
Journal: SCIENCE
Volume: 277
Page: 936-938
Year: 1997
Addresses:

***Article 6
Total Cites: 366
Article Title: CATALYTIC ASYMMETRIC OXIDATIONS USING OPTICALLY-ACTIVE (SALEN)MANGANESE(III) COMPLEXES AS CATALYSTS
Authors: Katsuki, T
Journal: COORDIN CHEM REV
Volume: 140
Page: 189-214
Year: 1995
Addresses:

***Article 7
Total Cites: 342
Article Title: Recent advances in asymmetric catalytic metal carbene transformations
Authors: Doyle, MP, Forbes, DC
Journal: CHEMICAL REVIEWS
Volume: 98
Page: 911-935
Year: 1998
Addresses:
· Univ Arizona, Dept Chem, Tucson, AZ, USA

***Article 8
Total Cites: 331
Article Title: Catalytic asymmetric organozinc additions to carbonyl compounds
Authors: Pu, L, Yu, HB
Journal: CHEMICAL REVIEWS
Volume: 101
Page: 757-824
Year: 2001
Addresses:
· Univ Virginia, Dept Chem, Charlottesville, VA, USA

***Article 9
Total Cites: 307
Article Title: Phosphinooxazolines - A new class of versatile, modular P,N-ligands for asymmetric catalysis
Authors: Helmchen, G, Pfaltz, A
Journal: ACCOUNTS CHEM RES
Volume: 33
Page: 336-345
Year: 2000
Addresses:
· Univ Heidelberg, Inst Organ Chem, Heidelberg, Germany
· Univ Basel, Dept Chem, Basel, Switzerland

***Article 10
Total Cites: 301
Article Title: Asymmetric catalysis by architectural and functional molecular engineering: Practical chemo- and stereoselective hydrogenation of ketones
Authors: Noyori, R, Ohkuma, T
Journal: ANGEW CHEM INT EDIT
Volume: 40
Page: 40-73
Year: 2001
Addresses:
· Nagoya Univ, Dept Chem, Chikusa Ku, Nagoya, Japan
· Nagoya Univ, Res Ctr Mat Sci, Chikusa Ku, Nagoya, Japan

***Article 11
Total Cites: 282
Article Title: The catalyst precursor, catalyst, and intermediate in the Ru-II-promoted asymmetric hydrogen transfer between alcohols and ketones
Authors: Haack, KJ, Hashiguchi, S, Fujii, A, Ikariya, T, Noyori, R
Journal: ANGEW CHEM INT EDIT
Volume: 36
Page: 285-288
Year: 1997
Addresses:
· RES DEV CORP JAPAN, ERATO, MOL CATALYSIS PROJECT, TOYOTA, JAPAN
· NAGOYA UNIV, DEPT CHEM, NAGOYA, JAPAN

***Article 12
Total Cites: 281
Article Title: Proline-catalyzed direct asymmetric aldol reactions
Authors: List, B, Lerner, RA, Barbas, CF
Journal: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume: 122
Page: 2395-2396
Year: 2000
Addresses:
· Scripps Res Inst, Skaggs Inst Chem Biol, La Jolla, CA, USA
· Scripps Res Inst, Dept Biol Mol, La Jolla, CA, USA

***Article 13
Total Cites: 278
Article Title: Nitrogen-containing ligands for asymmetric homogeneous and heterogeneous catalysis
Authors: Fache, F, Schulz, E, Tommasino, ML, Lemaire, M
Journal: CHEMICAL REVIEWS
Volume: 100
Page: 2159-2231
Year: 2000
Addresses:
· UCBL, UMR 5622, Lab Catalyse & Synthese Organ, CPE, Villeurbanne, France

***Article 14
Total Cites: 253
Article Title: ASYMMETRIC TRANSFER HYDROGENATION OF AROMATIC KETONES CATALYZED BY CHIRAL RUTHENIUM(II) COMPLEXES
Authors: Hashiguchi, S, Fujii, A, Takehara, J, Ikariya, T, Noyori, R
Journal: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume: 117
Page: 7562-7563
Year: 1995
Addresses:
· RES DEV CORP JAPAN, ERATO MOLEC CATALYSIS PROJECT, TOYOTA, JAPAN
· NAGOYA UNIV, DEPT CHEM, CHIKUSA KU, NAGOYA, JAPAN

***Article 15
Total Cites: 244
Article Title: Asymmetric catalysis of epoxide ring opening reactions
Authors: Jacobsen, EN
Journal: ACCOUNTS CHEM RES
Volume: 33
Page: 421-431
Year: 2000
Addresses:
· Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA, USA

***Article 16
Total Cites: 235
Article Title: Catalytic asymmetric aminohydroxylation (AA) of olefins
Authors: Li, GG, Chang, HT, Sharpless, KB
Journal: ANGEW CHEM INT EDIT
Volume: 35
Page: 451-454
Year: 1996
Addresses:
· Scripps Res Inst, DEPT CHEM, LA JOLLA, CA, USA

***Article 17
Total Cites: 223
Article Title: Palladium-catalyzed asymmetric allylic amination using ferrocenyl pyrazole ligands: Steric control of eta(3)-allyl configuration and site-selective nucleophilic attack
Authors: Togni, A, Burckhardt, U, Gramlich, V, Pregosin, PS, Salzmann, R
Journal: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume: 118
Page: 1031-1037
Year: 1996
Addresses:
· ETH ZENTRUM, INST CRYSTALLOG & PETROG, ZURICH, SWITZERLAND

***Article 18
Total Cites: 220
Article Title: Progress in asymmetric heterogeneous catalysis: Design of novel chirally modified platinum metal catalysts
Authors: Baiker, A
Journal: JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL
Volume: 115
Page: 473-493
Year: 1997
Addresses:

***Article 19
Total Cites: 208
Article Title: Ruthenium(II)-catalyzed asymmetric transfer hydrogenation of ketones using a formic acid-triethylamine mixture
Authors: Fujii, A, Hashiguchi, S, Uematsu, N, Ikariya, T, Noyori, R
Journal: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume: 118
Page: 2521-2522
Year: 1996
Addresses:
· RES DEV CORP JAPAN, ERATO, MOL CATALYSIS PROJECT, TOYOTA, JAPAN

***Article 20
Total Cites: 199
Article Title: Schiff base catalysts for the asymmetric Strecker reaction identified and optimized from parallel synthetic libraries
Authors: Sigman, MS, Jacobsen, EN
Journal: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume: 120
Page: 4901-4902
Year: 1998
Addresses:
· Harvard Univ, Dept Chem & Biol Chem, Cambridge, MA, USA

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3楼2007-05-30 18:23:21

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Angewandte Chemie

Asymmetric Synthesis Recent Advances in Asymmetric Phase-Transfer Catalysis
Takashi Ooi and Keiji Maruoka*

From the Contents
1. Introduction 4223
2. General Mechanism of Asymmetric
Phase-Transfer Catalysis 4224
3. Alkylation 4225
4. Michael Addition 4251
5. Aldol and Related Reactions 4257
6. Darzens Reaction 4257
7. Neber Rearrangement 4258
8. Horner–Wadsworth–Emmons Reaction 4259
9. Cyclopropanation 4259
10. Epoxidation 4259
11. Aziridination 4261
12. Oxidation 4262
13. Reduction 4262
14. Fluorination 4263
15. Sulfenylation 4263
16. Cyanation 4263
17. Conclusions 4263
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