Polymeric Chiral Catalyst Design and Chiral Polymer Synthesis

Herausgeber: Itsuno, Shinichi

• Gebundenes Buch

Produktbeschreibung

This book reviews chiral polymer synthesis and its application to asymmetric catalysis. It features the design and use of polymer-immobilized catalysts and methods for their design and synthesis. Chapters cover peptide-catalyzed and enantioselective synthesis, optically-active polymers, and continuous flow processes. It collects recent advances in an important field of polymer and organic chemistry, with leading researchers explaining applications in academic and industry R & D.

Produktdetails

• Verlag: John Wiley & Sons / Wiley
• Seitenzahl: 522
• Erscheinungstermin: 21. September 2011
• Englisch
• Abmessung: 236mm x 160mm x 30mm
• Gewicht: 953g
• ISBN-13: 9780470568200
• ISBN-10: 0470568208
• Artikelnr.: 33136950

Autorenporträt

Shinichi Itsuno, PhD, is a Professor at Toyohashi University of Technology. His research focuses on the interface between organic chemistry and polymer chemistry, and is especially concerned with asymmetric synthesis, reactive polymers, and new polymer synthesis. Dr. Itsuno has written over a hundred papers, as well as thirty book chapters.

Inhaltsangabe

PREFACE xiii FOREWORD xvii CONTRIBUTORS xix 1 An Overview of Polymer-Immobilized Chiral Catalysts and Synthetic Chiral Polymers 1 Shinichi Itsuno 1.1 Introduction
1 1.2 Polymeric Chiral Catalyst
2 1.3 Synthesis of Optically Active Polymers
8 2 Polymer-Immobilized Chiral Organocatalyst 17 Naoki Haraguchi and Shinichi Itsuno 2.1 Introduction
17 2.2 Synthesis of Polymer-immobilized Chiral Organocatalyst
18 2.3 Polymer-immobilized Cinchona Alkaloids
22 2.4 Other Polymer-immobilized Chiral Basic Organocatalysts
27 2.5 Polymer-immobilized Cinchona Alkaloid Quaternary Ammonium Salts
28 2.6 Polymer-immobilized MacMillan Catalysts
35 2.7 Polymer-immobilized Pyrrolidine Derivatives
42 2.8 Other Polymer-immobilized Chiral Quaternary Ammonium Salts
46 2.9 Polymer-immobilized Proline Derivatives
46 2.10 Polymer-immobilized Peptides and Poly(amino acid)s
50 2.11 Polymer-immobilized Chiral Acidic Organocatalysts
50 2.12 Helical Polymers as Chiral Organocatalysts
51 2.13 Cascade Reactions Using Polymer-immobilized Chiral Organocatalysts
52 2.14 Conclusions
54 3 Asymmetric Synthesis Using Polymer-Immobilized Proline Derivatives 63 Michelangelo Gruttadauria, Francesco Giacalone, and Renato Noto 3.1 Introduction
63 3.2 Polymer-supported Proline
66 3.3 Polymer-supported Prolinamides
73 3.4 Polymer-supported Proline-Peptides
75 3.5 Polymer-supported Pyrrolidines
78 3.6 Polymer-supported Prolinol and Diarylprolinol Derivatives
80 3.7 Conclusions and Outlooks
84 4 Peptide-Catalyzed Asymmetric Synthesis 91 Kazuaki Kudo and Kengo Akagawa 4.1 Introduction
91 4.2 Poly(amino acid) Catalysts
94 4.3 Tri- and Tetrapeptide Catalysts
99 4.4 Longer Peptides with a Secondary Structure
110 4.5 Others
118 4.6 Conclusions and Outlooks
119 5 Continuous Flow System using Polymer-Supported Chiral Catalysts 125 Santiago V. Luis and Eduardo Garc1a-Verdugo 5.1 Introduction
125 5.2 Asymmetric Polymer-supported, Metal-based Catalysts and Reagents
132 5.3 Polymer-supported Asymmetric Organocatalysts
147 5.4 Polymer-supported Biocatalysts
151 5.5 Conclusions
152 6 Chiral Synthesis on Polymer Support: A Combinatorial Approach 157 Deepak B. Salunke and Chung-Ming Sun 6.1 Introduction
157 6.2 Chiral Synthesis of Complex Polyfunctional Molecules on Polymer Support
160 6.3 Conclusions
194 7 Synthesis and Application of Helical Polymers with Macromolecular Helicity Memory 201 Hiroki Iida and Eiji Yashima 7.1 Introduction
201 7.2 Macromolecular Helicity Memory
203 7.3 Enantioselective Reaction Assisted by Helical Polymers with Helicity Memory
218 7.4 Conclusions
219 8 Poly(isocyanide)s, Poly(quinoxaline-2,3-diyl)s, and Related Helical Polymers Used as Chiral Polymer Catalysts in Asymmetric Synthesis 223 Yuuya Nagata and Michinori Suginome 8.1 Introduction
223 8.2 Asymmetric Synthesis of Poly(isocyanide)s
224 8.3 Asymmetric Synthesis of Poly(quinoxaline)s
244 8.4 Enantioselective Catalysis using Helical Polymers
255 8.5 Conclusions
262 9 C2 Chiral Biaryl Unit-Based Helical Polymers and Their Application to Asymmetric Catalysis 267 Takeshi Maeda and Toshikazu Takata 9.1 Introduction
267 9.2 Synthesis of C2 Chiral Unit-based Helical Polymers
269 9.3 Asymmetric Reactions Catalyzed by Helical Polymer Catalysts
282 9.4 Conclusions
289 10 Immobilization of Multicomponent Asymmetric Catalysts (MACs) 293 Hiroaki Sasai and Shinobu Takizawa 10.1 Introduction
293 10.2 Dendrimer-Supported and Dendronized Polymer-supported MACs
294 10.3 Nanoparticles as Supports for Chiral Catalysts [13]
302 10.4 The Catalyst Analog Approach [24]
311 10.5 Metal-bridged Polymers as Heterogeneous Catalysts: An Immobilization Method for MACs Without Using Any Support [26]
314 10.6 Conclusion
318 11 Optically Active Polymer and Dendrimer Synthesis and Their Use in Asymmetric Synthesis 323 Qiao-Sheng Hu and Lin Pu 11.1 Introduction
323 11.2 Synthesis and Application of BINOL
BINAP-based Optically Active Polymers
324 11.3 Synthesis and Application of Optically Active Dendrimers
355 11.4 Conclusions
360 12 Asymmetric Polymerizations of N-Substituted Maleimides 365 Kenjiro Onimura and Tsutomu Oishi 12.1 Introduction
365 12.2 Chirality of 1-Mono- or 1,1-Disubstituted and 1,2-Disubstituted Olefins
365 12.3 Asymmetric Polymerizations of Achiral N-Substituted Maleimides
368 12.4 Anionic Polymerization Mechanism of RMI
371 12.5 Asymmetric Polymerizations of Chiral N-Substituted Maleimides
372 12.6 Structure and Absolute Stereochemistry of Poly(RMI)
373 12.7 Asymmetric Radical Polymerizations ofN-Substituted Maleimides
378 12.8 Chiral Discrimination Using Poly(RMI)
378 12.9 Conclusions
384 13 Synthesis of Hyperbranched Polymer Having Binaphthol Units via Oxidative Cross-Coupling Polymerization 389 Shigeki Habaue 13.1 Introduction
389 13.2 Oxidative Cross-coupling Reaction between 2-Naphthol and 3-Hydroxy-2-naphthoate
391 13.3 Oxidative Cross-coupling Polymerization Affording Linear Poly(binaphthol)
392 13.4 Oxidative Cross-coupling Polymerization Leading to a Hyperbranched Polymer
396 13.5 Photoluminescence Properties of Hyperbranched Polymers
400 13.6 Conclusions
403 14 Optically Active Polyketones 407 Kyoko Nozaki 14.1 Introduction
407 14.2 Asymmetric Synthesis of Isotactic Poly(propylene-alt-co)
409 14.3 Asymmetric Synthesis of Isotactic Syndiotactic Poly(styrene-alt-co)
411 14.4 Asymmetric Terpolymers Consisting of Two Kinds of Olefins and Carbon Monoxide
413 14.5 Asymmetric Polymerization of Other Olefins with CO
414 14.6 Chemical Transformations of Optically Active Polyketones
415 14.7 Conformational Studies on the Optically Active Polyketones
416 14.8 Conclusions
419 15 Synthesis and Function of Chiral p-Conjugated Polymers from Phenylacetylenes 423 Toshiki Aoki, Takashi Kaneko, and Masahiro Teraguchi 15.1 Introduction
423 15.2 Helix-sense-selective Polymerization (HSSP) of Substituted Phenylacetylenes and Function of the Resulting One-handed Helical Poly(phenylacetylene)s
425 15.3 Chiral Desubstitution of Side Groups in Membrane State
439 15.4 Synthesis of Chiral Polyradicals
446 16 P-Stereogenic Oligomers, Polymers, and Related Cyclic Compounds 457 Yasuhiro Morisaki and Yoshiki Chujo 16.1 Introduction
457 16.2 P-Stereogenic Oligomers Containing Chiral "P" Atoms in the Main Chain
458 16.3 P-Stereogenic Polymers Containing Chiral "P" Atoms in the Main Chain
470 16.4 Cyclic Phosphines Using P-Stereogenic Oligomers as Building Blocks
475 16.5 Conclusions
485 INDEX 489