05246nam 2200661 a 450 991082827260332120240313160437.03-527-65671-53-527-65673-11-299-40214-33-527-65674-X(CKB)2550000001017926(EBL)1134690(OCoLC)829279532(SSID)ssj0000904843(PQKBManifestationID)11493074(PQKBTitleCode)TC0000904843(PQKBWorkID)10925564(PQKB)11648656(MiAaPQ)EBC1134690(Au-PeEL)EBL1134690(CaPaEBR)ebr10680785(CaONFJC)MIL471464(PPN)224482882(EXLCZ)99255000000101792620130409d2013 uy 0engur|n|---|||||txtccrModern methods in stereoselective aldol reactions /edited by Rainer Mahrwald1st ed.Weinheim Wiley-VCH20131 online resource (552 p.)Description based upon print version of record.3-527-33205-7 Includes bibliographical references and index.Modern Methods in Stereoselective Aldol Reactions; Contents; Preface; List of Contributors; 1 Stereoselective Acetate Aldol Reactions; 1.1 Introduction; 1.2 Mukaiyama Aldol Reaction; 1.2.1 Concept and Mechanism; 1.2.2 Chiral Auxiliaries; 1.2.3 Chiral Methyl Ketones; 1.2.4 Chiral Aldehydes; 1.2.4.1 1,2-Asymmetric Induction; 1.2.4.2 1,3-Asymmetric Induction; 1.2.4.3 Merged 1,2- and 1,3-Asymmetric Induction; 1.2.5 Chiral Lewis Acids; 1.2.6 Chiral Lewis Bases; 1.3 Metal Enolates; 1.3.1 Concept and Mechanism; 1.3.2 Chiral Auxiliaries; 1.3.3 Stoichiometric Lewis Acids; 1.3.4 Catalytic Lewis Acids1.3.5 Chiral Aldehydes1.3.6 Chiral Methyl Ketones; 1.3.6.1 a-Methyl Ketones; 1.3.6.2 a-Hydroxy Ketones; 1.3.6.3 b-Hydroxy Ketones; 1.3.6.4 b-Hydroxy a-Methyl Ketones; 1.3.6.5 a,b-Dihydroxy Ketones; 1.3.6.6 Remote Stereocontrol; 1.4 Conclusions; References; 2 The Vinylogous Mukaiyama Aldol Reaction in Natural Product Synthesis; 2.1 Introduction; 2.2 Aldehyde-Derived Silyl Dienol Ethers; 2.2.1 Aldehyde-Derived Silyl Dienol Ethers - Diastereoselective Processes; 2.2.2 Aldehyde-Derived Silyl Dienol Ethers - Enantioselective Processes; 2.3 Ester-Derived Silyl Dienol Ethers2.3.1 Ester-Derived Silyl Dienol Ethers - Diastereoselective Processes2.3.2 Ester-Derived Silyl Dienol Ethers - Enantioselective Processes; 2.3.3 Ester-Derived Silyl Dienol Ethers - Enantioselective and Substrate-Controlled Processes; 2.4 Amide-Derived Silyl Dienol Ethers - Vinylketene Silyl N,O-Acetals; 2.4.1 Model Systems - Kobayashi's Pioneering Studies; 2.4.2 Total Syntheses; 2.5 Acyclic Acetoacetate-Derived Silyl Dienolates - Chan's Diene; 2.5.1 Chan's Diene in Diastereoselective Processes; 2.5.2 Chan's Diene in Enantioselective Processes2.5.3 Chan's Diene in Enantioselective and Substrate-Controlled Processes2.6 Cyclic Acetoacetate-Derived Dienolates; 2.6.1 Cyclic Acetoacetate-Derived Dienolates - Diastereoselective Processes; 2.6.2 Cyclic Acetoacetate-Derived Dienolates - Enantioselective Processes; 2.6.3 Cyclic Acetoacetate-Derived Dienolates - Enantioselective and Substrate-Controlled Processes; 2.7 Furan-Derived Silyloxy Dienes; 2.7.1 Furan-Derived Silyloxy Dienes - Diastereoselective Processes; 2.7.2 Furan-Derived Silyloxy Dienes - Enantioselective Processes2.7.3 Furan-Derived Silyloxy Dienes - Enantioselective and Substrate-Controlled Processes2.8 Pyrrole-Based 2-Silyloxy Dienes; 2.9 Comparison with Other Methods; References; 3 Organocatalyzed Aldol Reactions; 3.1 Introduction; 3.2 Proline as Organocatalyst; 3.2.1 Intramolecular Reactions; 3.2.1.1 Intramolecular Proposed Mechanism; 3.2.1.2 Application to Natural Product Synthesis; 3.2.2 Intermolecular Reactions; 3.2.2.1 Ketones as Source of Nucleophile; 3.2.2.2 Aldehydes as Source of Nucleophile; 3.2.2.3 Intermolecular Reaction Mechanism; 3.2.2.4 Application to Natural Product Synthesis3.3 Proline Derivatives as OrganocatalystsThis sequel to the highly successful and much appreciated ""Modern Aldol Reactions"" continues to provide a systematic overview of methodologies for installing a required configuration during an aldol addition step, but shifts the focus so as to cover the latest developments.As such, it presents a set of brand new tools, including vinylogous Mukaiyama-aldol reactions, substrate-controlled aldol reactions and asymmetric induction in aldol additions. Furthermore, novel developments in existing stereoselective aldol additions are described, such as the deployment of supersilyl groups or organAldol condensationAldehydesAldol condensation.Aldehydes.547.036Mahrwald Rainer929216MiAaPQMiAaPQMiAaPQBOOK9910828272603321Modern methods in stereoselective aldol reactions3918715UNINA