LEADER 05262nam 2200613Ia 450 001 9910877601003321 005 20200520144314.0 010 $a1-280-85406-5 010 $a9786610854066 010 $a3-527-60685-8 010 $a3-527-60697-1 035 $a(CKB)1000000000376397 035 $a(EBL)481400 035 $a(OCoLC)70049971 035 $a(SSID)ssj0000231443 035 $a(PQKBManifestationID)11207808 035 $a(PQKBTitleCode)TC0000231443 035 $a(PQKBWorkID)10207380 035 $a(PQKB)10279941 035 $a(MiAaPQ)EBC481400 035 $a(EXLCZ)991000000000376397 100 $a20050207d2005 uy 0 101 0 $aeng 135 $aur|n|---||||| 181 $ctxt 182 $cc 183 $acr 200 00$aQuaternary stereocenters $echallenges and solutions for organic synthesis /$fedited by Jens Christoffers, Angelika Baro 210 $aWeinheim $cWiley-VCH ;$aChichester $cJohn Wiley$dc2005 215 $a1 online resource (362 p.) 300 $aDescription based upon print version of record. 311 $a3-527-31107-6 320 $aIncludes bibliographical references and index. 327 $aQuaternary Stereocenters; Contents; Foreword; Preface; List of Contributors; Symbols and Abbreviations; 1 Important Natural Products; 1.1 Introduction; 1.2 Alkylation of Tertiary Carbon Centers; 1.3 Cycloaddition to Alkenes; 1.3.1 Diels-Alder Reaction; 1.3.2 Other Types of Cycloaddition; 1.4 Rearrangement Reactions; 1.5 Carbometallation Reactions; 1.5.1 Addition of a Carbon Nucleophile to a ?,?-Disubstituted ?,?-Unsaturated Enone; 1.5.2 Asymmetric and Diastereomeric Addition of a Carbon Nucleophile to Unactivated Alkenes Catalyzed by Palladium [42]; 1.6 C-H Functionalization Reactions 327 $a1.7 Asymmetric Modification of Enantiotopic/Diastereotopic Substituents of Quaternary Carbon Centers1.8 Summary; 2 Important Pharmaceuticals and Intermediates; 2.1 The Chirality of Drugs and Agrochemicals; 2.2 Steroids; 2.3 Pharmaceuticals and Agrochemicals Based on ?-Dialkylated Amino Acids; 2.4 Azole Antimycotics; 2.5 Alkaloids; 2.6 HIV Inhibitors; 2.7 ?-Lactam Antibiotics; 2.8 The Tetracyclines; 2.9 Summary and Outlook; 3 Aldol Reactions; 3.1 Introduction; 3.2 Metal Enolates; 3.2.1 Lithium Enolates; 3.2.2 Titanium and Zirconium Enolates; 3.2.3 Boron Enolates; 3.3 Catalytic Aldol Additions 327 $a3.3.1 Fluoride-ion-mediated Aldol Addition3.3.2 Lewis-acid-mediated Mukaiyama-type Aldol Reactions; 3.3.3 Direct Aldol Additions; 3.3.4 Organocatalysis; 3.3.5 Enzyme and Antibody Catalysis; 3.4 Conclusions; 3.5 Note Added in Proof; 4 Michael Reactions and Conjugate Additions; 4.1 Introduction; 4.2 Chiral Bro?nstedt Bases; 4.2.1 Cinchona Alkaloids; 4.2.2 Polymer-bound Alkaloids; 4.2.3 Organocatalysis; 4.2.4 Miscellaneous Examples; 4.3 Chiral Metal Complexes; 4.3.1 Cobalt and Copper Catalysis; 4.3.2 Rhodium Catalysis; 4.3.3 Heterobimetallic Catalysis; 4.3.4 Miscellaneous Examples 327 $a4.4 Chiral Auxiliaries4.4.1 ?-Phenethylamine; 4.4.2 L-Valine Ester; 4.4.3 L-Valine Diethylamide; 4.4.4 Miscellaneous Examples; 5 Rearrangement Reactions; 5.1 Introduction; 5.2 Applications; 5.2.1 The Claisen Rearrangement; 5.2.2 The Overman Rearrangement; 5.2.3 The Cope Rearrangement; 5.2.4 The Wittig Rearrangement; 5.2.5 Semipinacol Rearrangements; 5.2.6 Miscellaneous; 5.3 Summary; 6 Cycloaddition Reactions; 6.1 Introduction; 6.2 [2+1] Cycloaddition Reactions; 6.3 [2+2] Cycloaddition Reactions; 6.4 1,3-Dipolar Cycloaddition Reactions; 6.4.1 Nitrone Cycloadditions 327 $a6.4.2 Other 1,3-Dipolar Cycloadditions6.5 Diels-Alder Reactions; 6.6 Hetero-Diels-Alder Reactions; 6.6.1 The Carbonyl Group as Dienophile; 6.6.2 ?,?-Unsaturated Carbonyl Derivatives as Heterodienes; 6.6.3 Imine Derivatives as Heterodienophiles; 6.7 Consecutive Cycloaddition Reactions; 7 Asymmetric Cross-coupling and Mizoroki-Heck Reactions; 7.1 The Asymmetric Heck Reaction; 7.1.1 Introduction; 7.1.2 Mizoroki-Heck Reaction Mechanism; 7.1.3 Asymmetric Formation of Quaternary Carbon Centers; 7.2 Metal-catalyzed Cross-coupling Reactions; 7.2.1 Palladium-catalyzed ?-Arylation 327 $a7.2.2 Palladium-catalyzed ?-Vinylation 330 $aFilling the gap in the literature, this book presents everything there is to know about this topic. By comprehensively covering the quaternary stereocenters found in a range of important and useful molecules in pharmaceutical and medicinal applications, as well as in thousands of natural products, the book provides the know-how chemists need to synthesize challenging molecules with numerous applications.A must for organic chemists in academia, the pharmaceutical industry and medicine.From the Contents:Important Natural ProductsImportant Pharmaceuticals and Intermediates 606 $aStereochemistry 606 $aOrganic compounds$xSynthesis 615 0$aStereochemistry. 615 0$aOrganic compounds$xSynthesis. 676 $a547.1223 701 $aChristoffers$b Jens$01761291 701 $aBaro$b Angelika$01761292 801 0$bMiAaPQ 801 1$bMiAaPQ 801 2$bMiAaPQ 906 $aBOOK 912 $a9910877601003321 996 $aQuaternary stereocenters$94200638 997 $aUNINA