LEADER 05163nam 2200673Ia 450 001 9911019754803321 005 20200520144314.0 010 $a9786612302497 010 $a9781282302495 010 $a1282302493 010 $a9783527627844 010 $a3527627847 010 $a9783527627851 010 $a3527627855 035 $a(CKB)1000000000807637 035 $a(EBL)482227 035 $a(OCoLC)476311833 035 $a(SSID)ssj0000338844 035 $a(PQKBManifestationID)11273753 035 $a(PQKBTitleCode)TC0000338844 035 $a(PQKBWorkID)10322948 035 $a(PQKB)11510578 035 $a(MiAaPQ)EBC482227 035 $a(Perlego)2769851 035 $a(EXLCZ)991000000000807637 100 $a20090803d2009 uy 0 101 0 $aeng 135 $aur|n|---||||| 181 $ctxt 182 $cc 183 $acr 200 00$aHydrogen bonding in organic synthesis /$fedited by Petri M. Pihko 210 $aWeinheim $cWiley-VCH$d2009 215 $a1 online resource (397 p.) 300 $aDescription based upon print version of record. 311 08$a9783527318957 311 08$a352731895X 320 $aIncludes bibliographical references and index. 327 $aHydrogen Bonding in Organic Synthesis; Contents; Preface; List of Contributors; 1: Introduction; 1.1 Introduction; 1.2 Hydrogen Bonding in Organic Synthesis; 2: Hydrogen-Bond Catalysis or Brønsted-Acid Catalysis? General Considerations; 2.1 Introduction; 2.2 What is the Hydrogen Bond?; 2.3 Hydrogen-Bond Catalysis or Brønsted-Acid Catalysis; 2.4 Brønsted-Acid Catalysis; 2.5 Hydrogen-Bond Catalysis; References; 3: Computational Studies of Organocatalytic Processes Based on Hydrogen Bonding; 3.1 Introduction; 3.1.1 Catalytic Functions of Hydrogen Bonds 327 $a3.2 Dynamic Kinetic Resolution (DKR) of Azlactones-Thioureas Can Act as Oxyanion Holes Comparable to Serine Hydrolases3.2.1 The Calculated Reaction Path of the Alcoholytic Ring Opening of Azlactones; 3.2.2 How Hydrogen Bonds Determine the Enantioselectivity of the Alcoholytic Azlactone Opening; 3.3 On the Bifunctionality of Chiral Thiourea-Tert-Amine-Based Organocatalysts: Competing Routes to C-C Bond Formation in a Michael Addition; 3.4 Dramatic Acceleration of Olefin Epoxidation in Fluorinated Alcohols: Activation of Hydrogen Peroxide by Multiple Hydrogen Bond Networks 327 $a3.4.1 Hydrogen Bond Donor Features of HFIP3.4.2 The Catalytic Activity of HFIP in the Epoxidation Reaction; 3.5 TADDOL-Promoted Enantioselective Hetero-Diels-Alder Reaction of Danishefsky's Diene with Benzaldehyde-Another Example for Catalysis by Cooperative Hydrogen Bonding; 3.6 Epilog; References; 4: Oxyanion Holes and Their Mimics; 4.1 Introduction; 4.1.1 What are Oxyanion Holes?; 4.1.2 Contributions of Oxyanion Holes to Catalysis; 4.1.3 Properties of Hydrogen Bonds of Oxyanion Holes; 4.2 A More Detailed Description of the Two Classes of Oxyanion Holes in Enzymes 327 $a4.2.1 A Historical Perspective4.2.2 Oxyanion Holes with Tetrahedral Intermediates; 4.2.3 Oxyanion Holes with Enolate Intermediates; 4.2.3.1 Examples of Enolate Oxyanion Holes; 4.3 Oxyanion Hole Mimics; 4.3.1 Mimics of Enzymatic Oxyanion Holes and Similar Systems; 4.3.2 Utilization of Oxyanion Holes in Enzymes for Other Reactions; 4.4 Concluding Remarks; Acknowledgments; References; 5: Brønsted Acids, H-Bond Donors, and Combined Acid Systems in Asymmetric Catalysis; 5.1 Introduction; 5.2 Brønsted Acid (Phosphoric Acid and Derivatives); 5.2.1 Binapthylphosphoric Acids; 5.2.1.1 Mannich Reaction 327 $a5.2.1.2 Hydrophosphonylation5.2.1.3 Friedel-Crafts; 5.2.1.4 Diels-Alder; 5.2.1.5 Miscellaneous Reactions; 5.2.1.6 Nonimine Electrophiles; 5.2.1.7 Transfer Hydrogenation; 5.2.2 Nonbinol-Based Phosphoric Acids; 5.2.3 N-Triflyl Phosphoramide; 5.2.4 Asymmetric Counteranion-Directed Catalysis; 5.3 N-H Hydrogen Bond Catalysts; 5.3.1 Guanidine Organic Base; 5.3.2 Ammonium Salt Catalysis; 5.3.3 Chiral Tetraaminophosphonium Salt; 5.4 Combined Acid Catalysis; 5.4.1 Brønsted-Acid-Assisted Brønsted Acid Catalysis; 5.4.1.1 Diol Activation of Carbonyl Electrophiles 327 $a5.4.1.2 Diol Activation of Other Electrophiles 330 $aThis first comprehensive overview of the rapidly growing field emphasizes the use of hydrogen bonding as a tool for organic synthesis, especially catalysis. As such, it covers such topics as enzyme chemistry, organocatalysis and total synthesis, all unified by the unique advantages of hydrogen bonding in the construction of complex molecules from simple precursors.Providing everything you need to know, this is a definite must for every synthetic chemist in academia and industry. 606 $aHydrogen bonding 606 $aOrganic compounds$xSynthesis 615 0$aHydrogen bonding. 615 0$aOrganic compounds$xSynthesis. 676 $a541.224 676 $a547.2 701 $aPihko$b Petri M$01839750 801 0$bMiAaPQ 801 1$bMiAaPQ 801 2$bMiAaPQ 906 $aBOOK 912 $a9911019754803321 996 $aHydrogen bonding in organic synthesis$94419092 997 $aUNINA