LEADER 05163nam 2200685Ia 450 001 9910831097003321 005 20230721022856.0 010 $a1-282-30251-5 010 $a9786612302510 010 $a3-527-62817-7 010 $a3-527-62818-5 035 $a(CKB)1000000000799486 035 $a(EBL)482311 035 $a(OCoLC)587391602 035 $a(SSID)ssj0000335806 035 $a(PQKBManifestationID)11229505 035 $a(PQKBTitleCode)TC0000335806 035 $a(PQKBWorkID)10279100 035 $a(PQKB)11759100 035 $a(MiAaPQ)EBC482311 035 $a(EXLCZ)991000000000799486 100 $a20090804d2009 uy 0 101 0 $aeng 135 $aur|n|---||||| 181 $ctxt 182 $cc 183 $acr 200 00$aCinchona alkaloids in synthesis and catalysis$b[electronic resource] $eligands, immobilization and organocatalysis /$fedited by Choong Eui Song 210 $aWeinheim $cWiley-VCH$dc2009 215 $a1 online resource (547 p.) 300 $aDescription based upon print version of record. 311 $a3-527-32416-X 320 $aIncludes bibliographical references and index. 327 $aCinchona Alkaloids in Synthesis and Catalysis: Ligands, Immobilization and Organocatalysis; Contents; Preface; Biography; List of Contributors; 1 An Overview of Cinchona Alkaloids in Chemistry; 1.1 Brief History; 1.2 Active Sites in Cinchona Alkaloids and Their Derivatives; 1.3 Structural Information on Cinchona Alkaloids; 1.4 How This Book Is Organized; References; Part One: Cinchona Alkaloid Derivatives as Chirality Inducers in Metal-Catalyzed Reactions; 2 Cinchona Alkaloids as Chirality Transmitters in Metal-Catalyzed Asymmetric Reductions; 2.1 Introduction 327 $a2.2 Homogeneous Systems for Ketone Reductions2.3 Heterogeneous Pt and Pd Catalysts Modified with Cinchona Alkaloids; 2.3.1 Background; 2.3.2 Catalysts; 2.3.3 Modifiers and Solvents; 2.3.4 Substrate Scope for Pt Catalysts; 2.3.4.1 ?-Keto Acid Derivatives; 2.3.4.2 ?,?-Diketo Esters; 2.3.4.3 Fluorinated Ketones; 2.3.4.4 ?-Keto Acetals; 2.3.4.5 ?-Keto Ethers; 2.3.4.6 Miscellaneous Ketones; 2.3.5 Substrate Scope for Pd Catalysts; 2.4 Industrial Applications; 2.5 Conclusions; References; 3 Cinchona Alkaloids as Chiral Ligands in Asymmetric Oxidations; 3.1 Introduction 327 $a3.2 Asymmetric Dihydroxylation of Alkenes3.2.1 Early Reactions; 3.2.2 Bisalkaloid Ligands; 3.2.3 Mechanism; 3.2.4 Variations; 3.2.5 Substrates and Selectivity; 3.2.5.1 Simple Alkenes; 3.2.5.2 Functionalized Alkenes; 3.2.5.3 Polyenes; 3.2.5.3.1 Nonconjugate Olefins; 3.2.5.3.2 Conjugated Polyenes; 3.2.5.4 Double Asymmetric Induction; 3.2.5.5 Resolutions; 3.2.6 Some Reactions of 1,2-Diols; 3.2.6.1 Cyclic Sulfates and Sulfites; 3.3 Aminohydroxylation; 3.4 Sulfur Oxidations; 3.5 Summary; References 327 $a4 Cinchona Alkaloids and their Derivatives as Chirality Inducers in Metal-Promoted Enantioselective Carbon-Carbon and Carbon-Heteroatom Bond Forming Reactions4.1 Introduction; 4.2 Nucleophilic Addition to Carbonyl or Imine Compounds; 4.2.1 Organozinc Addition; 4.2.1.1 Dialkylzinc Addition to Aldehydes; 4.2.1.2 Dialkylzinc Addition to Imines; 4.2.1.3 Addition of Alkynylzincs to Carbonyls; 4.2.2 Asymmetric Reformatsky Reaction; 4.2.3 Indium-Mediated Addition; 4.2.4 Asymmetric Cyanation; 4.2.4.1 Cyanohydrin Synthesis; 4.2.4.2 Strecker Synthesis 327 $a4.2.5 Reactions of Chiral Ammonium Ketene Enolates as Nucleophiles with Different Electrophiles4.2.5.1 Lewis Acid Assisted Nucleophilic Addition of Ketenes (or Sulfenes) to Aldehydes: ?-Lactone and ?-Sultone Synthesis; 4.2.5.2 Lewis Acid Assisted Nucleophilic Addition of Ketenes to Imines: ?-Lactam Synthesis; 4.2.5.3 Applications of Chiral Ketene Enolates to Formal [4 + 2] type Cyclization; 4.2.6 Aza-Henry Reaction; 4.2.7 Enantioselective Hydrophosphonylation; 4.3 Miscellaneous Reactions; 4.3.1 Claisen Rearrangements; 4.3.2 Pd-Catalyzed Asymmetric Allylic Substitutions 327 $a4.3.3 Pauson-Khand Reaction 330 $aThis comprehensive review of cinchona-based chiralilty inducers and their applications covers every topic, including ligands, immobilization and organocatalysis. Each chapter summarizes the scope and limitations of the new methods and technologies, while the final chapter contains carefully selected working procedures of cinchona alkaloid-promoted reactions organized according to reaction type. Invaluable reading for anyone wanting to learn about the current state of this hot topic. 606 $aCinchona alkaloids 606 $aChirality 606 $aOrganic compounds$xSynthesis 606 $aCatalysis 615 0$aCinchona alkaloids. 615 0$aChirality. 615 0$aOrganic compounds$xSynthesis. 615 0$aCatalysis. 676 $a547.215 676 $a547.7 686 $aVK 5500$2rvk 686 $aVK 8620$2rvk 701 $aSong$b Choong Eui$01714603 801 0$bMiAaPQ 801 1$bMiAaPQ 801 2$bMiAaPQ 906 $aBOOK 912 $a9910831097003321 996 $aCinchona alkaloids in synthesis and catalysis$94108561 997 $aUNINA