LEADER 05112nam 2200601 a 450 001 9910146238103321 005 20220609161331.0 010 $a1-280-52047-7 010 $a9786610520473 010 $a3-527-60538-X 010 $a3-527-60188-0 035 $a(CKB)1000000000019365 035 $a(EBL)482328 035 $a(OCoLC)68919709 035 $a(SSID)ssj0000204267 035 $a(PQKBManifestationID)11181348 035 $a(PQKBTitleCode)TC0000204267 035 $a(PQKBWorkID)10196084 035 $a(PQKB)10443914 035 $a(MiAaPQ)EBC482328 035 $a(PPN)243300557 035 $a(EXLCZ)991000000000019365 100 $a20040608d2004 uy 0 101 0 $aeng 135 $aur|n|---||||| 181 $ctxt 182 $cc 183 $acr 200 00$aModern carbonyl olefination$b[electronic resource] /$fTakeshi Takeda (ed.) 210 $aWeinheim $cWiley-VCH$dc2004 215 $a1 online resource (367 p.) 300 $aDescription based upon print version of record. 311 $a3-527-30634-X 320 $aIncludes bibliographical references and index. 327 $aModern Carbonyl Olefination; Contents; Preface; List of Authors; 1 The Wittig Reaction; 1.1 Introduction; 1.2 The ""Classic"" Wittig Reaction; 1.2.1 Mechanism and Stereoselectivity; 1.2.2 Nature of the Ylide and Carbonyl Compound; 1.2.3 Reagents and Reaction Conditions; 1.3 Horner-Wadsworth-Emmons Reaction; 1.3.1 Mechanism and Stereochemistry; 1.3.2 Reagents and Reaction Conditions; 1.4 Horner-Wittig (HW) Reaction; 1.4.1 Mechanism and Stereochemistry; 1.4.2 Reagents and Reaction Conditions; 1.5 Conclusion; References; 2 The Peterson and Related Reactions; 2.1 Introduction 327 $a2.2 Stereochemistry and the Reaction Mechanism of the Peterson Reaction2.2.1 Stereochemistry and the Reaction Mechanism of the Peterson Reaction of ?-Hydroxyalkylsilanes; 2.2.1.1 Stepwise Mechanism; 2.2.1.2 Reaction Mechanism via a 1,2-Oxasiletanide; 2.2.2 Reaction Mechanism of the Addition Step of an ?-Silyl Carbanion to a Carbonyl Compound; 2.2.2.1 Approach Control of the Transition State; 2.2.2.2 Concerted Mechanism; 2.2.2.3 Chelation Control Mechanism; 2.2.3 Theoretical Calculations on the Reaction Mechanism; 2.2.4 Convergently Stereoselective Peterson Reactions 327 $a2.3 Generation of ?-Silyl Carbanions and their Peterson Reactions2.3.1 Generation of ?-Silyl Carbanions from ?-Silylalkyl Halides; 2.3.1.1 Generation of ?-Silyl Grignard Reagents from ?-Silylalkyl Halides; 2.3.1.2 Generation of ?-Silyl Alkyllithium Reagents from ?-Silylalkyl Halides; 2.3.1.3 Synthesis of Terminal Alkenes by the Use of ?-Silyl Carbanions Generated from ?-Silylalkyl Halides; 2.3.1.4 Reactions of ?-Silyl Carbanions Generated from ?-Silylalkyl Halides with Esters, Carboxylic Acids, and Acetals; 2.3.1.5 The Reformatsky-Peterson Reactions of ?-Silylalkyl Halides 327 $a2.3.2 Generation of ?-Silyl Carbanions by Deprotonation of Alkylsilanes2.3.2.1 Generation of ?-Silyl Carbanions Bearing an Aryl or a Heteroaryl Group; 2.3.2.2 Generation of ?-Silyl Carbanions Bearing an Alkoxy Group; 2.3.2.3 Generation of ?-Silyl Carbanions Bearing a Nitrogen-Containing Group; 2.3.2.4 Generation of ?-Silyl Carbanions Bearing a Sulfur-Containing Group; 2.3.2.5 Generation of ?-Silyl Carbanions Bearing a Phosphorus-Containing Group; 2.3.2.6 Generation of ?-Silyl Carbanions Bearing a Halogen Group; 2.3.2.7 Generation of ?-Silyl Carbanions from ?-Silyl Ketones 327 $a2.3.2.8 Generation of ?-Silyl Carbanions Bearing an Ester Group2.3.2.9 Generation of ?-Silyl Carbanions Bearing a Lactone Group; 2.3.2.10 Generation of ?-Silyl Carbanions Bearing Thiocarboxylate or Dithiocarboxylate Ester Groups; 2.3.2.11 Generation of ?-Silyl Carbanions Bearing an Imino Group; 2.3.2.12 Generation of ?-Silyl Carbanions Bearing an Amide Group; 2.3.2.13 Generation of ?-Silyl Carbanions Bearing a Cyano Group; 2.3.2.14 Generation of ?-Silyl Carbanions from Allylsilanes; 2.3.2.15 Generation of ?-Silyl Carbanions from Propargylsilanes 327 $a2.3.3 Generation of ?-Silyl Carbanions by Substitution of a Heteroatom 330 $aWhile this important reaction class is among the most important and most widely used in organic chemistry, this is the first book to summarize the many different olefination methods, including:* Wittig reaction* Peterson reaction* Julia olefination * Utilizing the Tebbe and related reagents* Low-valent chromium, zinc or titanium mediated olefination* McMurry coupling plus the related reactions in each case and the application to asymmetric synthesis. It thus collates in one ready reference the current level of knowledge as well as new developments in this constantly 606 $aCarbonyl compounds 615 0$aCarbonyl compounds. 676 $a547.036 676 $a547.05621046 701 $aTakeda$b Takeshi$0975550 801 0$bMiAaPQ 801 1$bMiAaPQ 801 2$bMiAaPQ 906 $aBOOK 912 $a9910146238103321 996 $aModern carbonyl olefination$92221370 997 $aUNINA