Polymeric chiral catalyst design and chiral polymer synthesis

著者

書誌事項

Polymeric chiral catalyst design and chiral polymer synthesis

edited by Shinichi Itsuno

Wiley, c2011

大学図書館所蔵 件 / 全6件

この図書・雑誌をさがす

注記

Includes bibliographical references and index

内容説明・目次

内容説明

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.

目次

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 Garcia-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

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