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9783527306831

Modern Rhodium-Catalyzed Organic Reactions

by ;
  • ISBN13:

    9783527306831

  • ISBN10:

    3527306838

  • Edition: 1st
  • Format: Hardcover
  • Copyright: 2005-03-04
  • Publisher: Wiley-VCH
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Summary

Rhodium has proven to be an extremely useful metal due to its ability to catalyze an array of synthetic transformations, with quite often-unique selectivity. Hydrogenation, C-H activation, allylic substitution, and numerous other reactions are catalyzed by this metal, which presumably accounts for the dramatic increase in the number of articles that have recently emerged on the topic.P. Andrew Evans, the editor of this much-needed book, has assembled an internationally renowned team to present the first comprehensive coverage of this important area. The book features contributions from leaders in the field of rhodium-catalyzed reactions, and thereby provides a detailed account of the most current developments, including: Rhodium-Catalyzed Asymmetric Hydrogenation (Zhang) Rhodium-Catalyzed Hydroborations and Related Reactions (Brown) Rhodium-Catalyzed Asymmetric Addition of Organometallic Reagents to Electron Deficient Olefins (Hayashi) Recent Advances in Rhodium(I)-Catalyzed Asymmetric Olefin Isomerization and Hydroacylation Reactions (Fu) Stereoselective Rhodium(I)-Catalyzed Hydroformylation and Silylformylation Reactions and Their Application to Organic Synthesis (Leighton) Carbon-Carbon Bond-Forming Reactions Starting from Rh-H or Rh-Si Species (Matsuda) Rhodium(I)-Catalyzed Cycloisomerization and Cyclotrimerization Reactions (Ojima) The Rhodium(I)-Catalyzed Alder-ene Reaction (Brummond) Rhodium-Catalyzed Nucleophilic Ring Cleaving Reactions of Allylic Ethers and Amines (Fagnou) Rhodium(I)-Catalyzed Allylic Substitution Reactions and their Applications to Target Directed Synthesis (Evans) Rhodium(I)-Catalyzed [2+2+1] and [4+1] Carbocyclization Reactions (Jeong) Rhodium(I)-Catalyzed [4+2] and [4+2+2] Carbocyclizations (Robinson) Rhodium(I)-Catalyzed [5+2], [6+2], and [5+2+1] Cycloadditions: New Reactions for Organic Synthesis (Wender) Rhodium(II)-Stabilized Carbenoids Containing both Donor and Acceptor Substituents (Davies) Chiral Dirhodium(II)Carboxamidates for Asymmetric Cyclopropanation and Carbon-Hydrogen Insertion Reactions (Doyle) Cyclopentane Construction by Rhodium(II)-Mediated Intramolecular C-H Insertion (Taber) Rhodium(II)-Catalyzed Oxidative Amination (DuBois) Rearrangement Processes of Oxonium and Ammonium Ylides Formed by Rhodium(II)-Catalyzed Carbene-Transfer (West) Rhodium(II)-Catalyzed 1,3-Dipolar Cycloaddition Reactions (Austin) Modern Rhodium-Catalyzed Organic Reactions is an essential reference text for researchers at all levels in the general area of organic chemistry. This book provides an invaluable overview of the most significant developments in this important area of research, and will no doubt be an essential text for researchers at academic institutions and professionals at pharmaceutical/agrochemical companies.

Author Biography

P. Andrew Evans is a Professor Department of Chemistry at Indiana University, Bloomington. He obtained a Ph.D from Cambridge University under the supervision of Professor Andrew B. Holmes, F.R.S, and was a NATO Postdoctoral Fellow at the University of Texas at Austin with Professor Philip D. Magnus, F.R.S. Professor Evans' research has been recognized on several occasions. Recent awards include a Camille Dreyfus Teacher-Scholar Award, a Johnson and Johnson Focused Giving Award and the Pfizer Award for Creativity in Organic Chemistry.

Table of Contents

Foreword.
Preface.
List of Contributors.
1 Rhodium-Catalyzed Asymmetric Hydrogenation (Yongxiang Chi, Wenjun Tang, and Xumu Zhang).
1.1 Introduction.
1.2 Chiral Phosphorous Ligands.
1.3 Applications of Chiral Phosphorous Ligands in Rhodium-Catalyzed Asymmetric Hydrogenation.
1.4 Conclusion.
1.5 References.
2 Rhodium-Catalyzed Hydroborations and Related Reactions (John M. Brown).
2.1 Introduction.
2.2 General Advances in Catalytic Hydroboration.
2.3 Advances in Asymmetric Hydroboration.
2.4 Catalytic Diboration of Alkenes.
2.5 Summary and Conclusions.
2.6 References.
3 Rhodium(I)-Catalyzed Asymmetric Addition of Organometallic Reagents to Electron-Deficient Olefins (Kazuhiro Yoshida and Tamio Hayashi).
3.1 Introduction.
3.2 Addition of Organoboron Reagents to α,β-Unsaturated Ketones.
3.3 Mechanism.
3.4 Addition of Organoboron Reagents to Other Electron-Deficient Olefins.
3.5 Addition of Organotin and -silicon Reagents.
3.6 New Aspects of Addition of Organoboron and -titanium Reagents.
3.7 Outlook.
3.8 References.
4 Recent Advances in Rhodium(I)-Catalyzed Asymmetric Olefin Isomerization and Hydroacylation Reactions (Gregory C. Fu).
4.1 Rhodium(I)-Catalyzed Asymmetric Isomerization of Olefins.
4.2 Rhodium(I)-Catalyzed Asymmetric Hydroacylation of Olefins and Alkynes with Aldehydes.
4.3 References.
5 Stereoselective Rhodium(I)-Catalyzed Hydroformylation and Silylformylation Reactions and their Application to Organic Synthesis (James L. Leighton).
5.1 Introduction.
5.2 Hydroformylation.
5.3 Silylformylation.
5.4 Conclusion.
5.5 References.
6 Carbon–Carbon Bond–Forming Reactions Starting from Rh–H or Rh–Si Species (Isamu Matsuda).
6.1 Introduction.
6.2 Background.
6.3 Design of Reactions Starting from Insertion into a Rh–H Bond.
6.4 Design of Reactions Starting from Insertion into a Rh–Si Bond.
6.5 Conclusion.
6.6 References.
7 Rhodium(I)-Catalyzed Cycloisomerization and Cyclotrimerization Reactions (Masaki Fujiwara and Iwao Ojima).
7.1 Introduction.
7.2 Carbocyclization.
7.3 Cascade Carbocyclization.
7.4 Carbonylative Carbocyclization.
7.5 Conclusion.
7.6 References.
8 The Rhodium(I)-Catalyzed Alder-Ene Reaction (Kay M. Brummond and Jamie M. McCabe).
8.1 Introduction.
8.2 Diene Alder-Ene Reactions.
8.3 Enyne Alder-Ene Reactions.
8.4 Allenyne Alder-Ene Reactions.
8.5 Kinetic Resolution.
8.6 Other Rhodium-Catalyzed Ene-Type Reactions.
8.7 Conclusion.
8.8 References.
9 Rhodium-Catalyzed Nucleophilic Ring Cleaving Reactions of Allylic Ethers and Amines (Keith Fagnou).
9.1 Introduction.
9.2 Seminal Work.
9.3 Asymmetric Reactions with Oxabicyclic Alkenes.
9.4 Azabicyclic Alkenes.
9.5 Properties of the PPF-P<sup>t</sup>Bu<sub>2</sub> Ligand.
9.6 Mechanistic Working Model.
9.7 Vinyl Epoxides.
9.8 Conclusion.
9.9 References.
10 Rhodium(I)-Catalyzed Allylic Substitution Reactions and their Applications to Target Directed Synthesis (David K. Leahy and P. Andrew Evans).
10.1 Introduction.
10.2 Regioselective Rhodium-Catalyzed Allylic Alkylation.
10.3 Enantiospecific Rhodium-Catalyzed Allylic Alkylation.
10.4 Enantioselective Rhodium-Catalyzed Allylic Alkylations.
10.5 Conclusion.
10.6 References.
11 Rhodium(I)-Catalyzed [2+2+1] and [4+1] Carbocyclization Reactions (Nakcheol Jeong).
11.1 General Introduction to Rhodium-Mediated Carbocyclizations.
11.2 [2+2+1] Carbocyclization.
11.3 [4+1] Carbocyclization.
11.4 Conclusion.
11.5 References.
12 Rhodium(I)-Catalyzed [4+2] and [4+2+2] Carbocyclizations (John E. Robinson).
12.1 Introduction.
12.2 Rhodium(I)-Catalyzed [4+2] Carbocyclization Reactions.
12.3 Rhodium(I)-Catalyzed [4+2+2] Carbocyclization Reactions.
12.4 References.
13 Rhodium(I)-Catalyzed [5+2], [6+2], and [5+2+1] Cycloadditions: New Reactions for Organic Synthesis (Paul A. Wender, Gabriel G. Gamber, and Travis J. Williams).
13.1 Introduction.
13.2 Cycloaddition Approaches to Seven-Membered Rings.
13.3 Design of a Transition Metal-Catalyzed [5+2] Cycloaddition of Vinylcyclopropanes and Π-Systems.
13.4 Intramolecular [5+2] Cycloadditions of VCPs.
13.5 Intermolecular [5+2] Cycloadditions of VCPs and Alkynes.
13.6 Cycloaddition Approaches for Eight-Membered Ring Synthesis.
13.7 Design and Development of [6+2] Cycloadditions of Vinylcyclobutanones.
13.8 Design and Development of Multi-component [5+2+1] Cycloadditions of VCPs, Alkynes, and CO.
13.9 Conclusion.
13.10 References.
14 Rhodium(II)-Stabilized Carbenoids Containing Both Donor and Acceptor Substituents (Huw M.L. Davies and Abbas M. Walji).
14.1 Introduction.
14.2 Cyclopropanation.
14.3 [3+4] Cycloaddition of Vinyl Carbenoids.
14.4 [3+2] Cycloaddition of Vinyl Carbenoids.
14.5 Ylide Transformations.
14.6 Si–H Insertion.
14.7 C–H Activation by Carbenoid-Induced C–H Insertion.
14.8 References.
15 Chiral Dirhodium(II) Carboxamidates for Asymmetric Cyclopropanation and Carbon–Hydrogen Insertion Reactions (Michael P. Doyle).
15.1 Introduction.
15.2 Catalytic Asymmetric Cyclopropanation and Cyclopropenation.
15.3 Catalytic Asymmetric Carbon–Hydrogen Insertion.
15.4 Summary.
15.5 References.
16 Cyclopentane Construction by Rhodium(II)-Mediated Intramolecular C–H Insertion (Douglass F. Taber and Pramod V. Joshi).
16.1 Introduction.
16.2 Background: Cyclization versus Elimination.
16.3 Beginnings of a Computational Approach.
16.4 Comparing and Contrasting Rhodium Catalysts: Four Dimensions of Reactivity.
16.5 Design of an Enantioselective Catalyst.
16.6 Conclusion.
16.7 References.
17 Rhodium(II)-Catalyzed Oxidative Amination (Christine G. Espino and Justin Du Bois).
17.1 Introduction.
17.2 Background.
17.3 Intermolecular C–H Amination with Rhodium(II) Catalysts.
17.4 Intermolecular C–H Amination with Other Metals.
17.5 Intramolecular C–H Amination with Rhodium(II) Catalysts.
17.6 Rhodium(II)-Catalyzed Olefin Aziridination.
17.7 Enantioselective C–H Insertion with Sulfamate Esters.
17.8 Mechanistic Investigations.
17.9 Summary and Outlook for Rhodium(II)-Catalyzed Nitrene Transfer.
17.10 Rhodium(II)-Catalyzed Olefin Diamination.
17.11 Applications of C–H Amination in Synthesis.
17.12 Conclusion.
17.13 References.
18 Rearrangement Processes of Oxonium and Ammonium Ylides Formed by Rhodium(II)-Catalyzed Carbene Transfer (Frederick G. West).
18.1 Introduction.
18.2 Oxonium Ylides.
18.3 Ammonium Ylides.
18.4 Conclusion.
18.5 References.
19 Rhodium(II)-Catalyzed 1,3-Dipolar Cycloaddition Reactions (Ruben M. Savizky and David J. Austin)
19.1 Rhodium(II) in 1,3-Dipole Formation.
19.2 Chemical Aspects of Rhodium-Mediated 1,3-Dipolar Cycloaddition.
19.3 Applications of Rhodium(II)-Mediated 1,3-Dipolar Cycloaddition.
19.4 Conclusion.
19.5 References.
Subject Index.

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