Classics in Stereoselective Synthesis

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Beschreibung Autorinnen & Autoren

Die wichtigsten und nützlichsten Methoden der modernen stereoselektiven Synthese sind in diesem Band zusammengefasst. Viele anschauliche Beispiele für die Darstellung von Wirkstoffen und Naturstoffen regen zur gezielten Abwandlung und Integration in eigene Synthesewege an. Dabei geht es den Autoren weniger darum, das Gebiet in seiner Gesamtheit darzustellen; vielmehr versuchen sie, die wirklich grundlegenden Ansätze auszuwählen, die jeder organische Synthesechemiker kennen und anwenden sollte.

MACROCYCLIC STEREOCONTROL Introduction Background Conformational Control in Medium-Sized Rings Asymmetric Synthesis with Medium-Sized Rings Case Studies in Natural Products Total Synthesis Macrocyclic Stereocontrol in Cyclic Peptides Appendix: Macrocycle Formation CARBONYL ADITION REACTIONS Introduction Non-Chelated 1,2-Asymmetric Induction and the Operation of Steric and Electronic Effects 1,2-Asymmetric Induction Predicated on Chelation Control 1,3-Asymmetric Induction from CBeta Stereogenic Centers Asymmetric Induction by Remote Stereocenters (Beyond 1,3-Induction) Catalytic Enantioselective Carbonyl Additions of Arganozinc Species Enantioselective Ketone Reduction Enzymatic Reduction of Ketones Enantioselective Formation of Cyanohydrins Enantioselective Alkyne Additions Asymmetric Carbonyl-Ene Reactions ALPHA-FUNCTIONALIZATIONS OF ENOLATES Introduction Diastereoselective Alpha-Alkylations of Chiral Enolates Heteroatom-Substituted Enolates Asymmetric Enolate Alkylations Using Chiral Auxiliaries Enantioselective Enolate Alkylations Alpha-Hydroxylations of Enolates Alpha-Halogenations of Enolates ALDOL REACTIONS Introduction Chiral Enolates Through the Use of Chiral Auxiliaries or Chiral Controller Groups Substrate Control with Chiral Carbonyl Compounds Catalytic Enantioselective Aldol Reactions ALLYLATIONS OF C=O BONDS Introduction Reactivity of Allylmetal Reagents Boronate Additions Enantioselective Additions of Optically Active Allylic Boron Reagents Diastereoselecive Allylations with Chiral Boron Reagents Mechanistic Aspects - Lewis Acid-Promoted Addition of Allylsilanes and Allylstannanes to Aldehydes Chelation Control in the Allylation of Alpha- and Beta-Alkoxy Aldehydes Allylchromium Reagents Diastereoselective Allylations with Chiral Silanes and Stannanes Catalytic Asymmetric Allylations CHIRAL ACETALS Introduction Diastereoselective Reactions of Chiral Acetals Glycosylations Spiroketals in Natural Product Synthesis ALKENE HYDROBORATION Introduction Hydroborations with Acyclic Stereocontrol Metal-Catalyzed Hydroborations Asymmetric Hydroborations with Chiral Boranes Catalytic Asymmetric Hydroboration, Hydrosilylation, and Hydroalumination REDUCTIONS OF OLEFINS Introduction Diastereoselective Olefin Reductions by Catalytic Hydrogenation Alternative Methods for Diastereoselective Olefin Reductions Catalytic Asymmetric Olefin Hydrogenations OXIDATIONS OF OLEFINS Introduction Diastereoselective Epoxidations Enantioselective Epoxidations Asymmetric Ring-Opening of Epoxides Synthesis of Aziridines Iodolactonizations and Other Olefin Cyclizations Induced by Electrophiles Diastereoselective Dihydroxylations of Olefins Enantioselective Dihydroxylations of Olefins Enantioselective Aminohydroxylation of Olefins AMINO ACIDS Introduction Enantioselective Hydrogenations of Alpha, Beta-Didehydroamino Acids Enolate Alkylations in the Presence of Chiral Auxiliaries Alkylation of Glycine Anion Equivalents in the Presence of Chiral Phase-Transfer Catalysts Enolate Aminations Enzymatic Syntheses of Alpha-Amino Acids Catalytic Asymmetric Strecker Reactions ADDITIONS TO C=N BONDS Introduction Substrate-Controlled Diastereoselective Additions to C=N Bonds Additions to Imine Derivatives Bearing N-Bound Auxiliaries Formation of Beta-Lactams Through Staudinger Reactions Intramolecular Diastereoselective Iminium Ion Cyclizations Pictet-Spengler Reactions Catalytic Asymmetric Reductions of Imines and Imine Derivatives Catalytic Enantioselective Mannich and Mannich-Type Reactions Enantioselective Additions of Carbon Nucleophiles to C=N Bonds CONJUGATE ADDITIONS Introduction Diastereoselective Conjugate Additions Diastereoselective Conjugate Additions with Use of Chiral

MACROCYCLIC STEREOCONTROL Introduction Background Conformational Control in Medium-Sized Rings Asymmetric Synthesis with Medium-Sized Rings Case Studies in Natural Products Total Synthesis Macrocyclic Stereocontrol in Cyclic Peptides Appendix: Macrocycle Formation CARBONYL ADITION REACTIONS Introduction Non-Chelated 1,2-Asymmetric Induction and the Operation of Steric and Electronic Effects 1,2-Asymmetric Induction Predicated on Chelation Control 1,3-Asymmetric Induction from CBeta Stereogenic Centers Asymmetric Induction by Remote Stereocenters (Beyond 1,3-Induction) Catalytic Enantioselective Carbonyl Additions of Arganozinc Species Enantioselective Ketone Reduction Enzymatic Reduction of Ketones Enantioselective Formation of Cyanohydrins Enantioselective Alkyne Additions Asymmetric Carbonyl-Ene Reactions ALPHA-FUNCTIONALIZATIONS OF ENOLATES Introduction Diastereoselective Alpha-Alkylations of Chiral Enolates Heteroatom-Substituted Enolates Asymmetric Enolate Alkylations Using Chiral Auxiliaries Enantioselective Enolate Alkylations Alpha-Hydroxylations of Enolates Alpha-Halogenations of Enolates ALDOL REACTIONS Introduction Chiral Enolates Through the Use of Chiral Auxiliaries or Chiral Controller Groups Substrate Control with Chiral Carbonyl Compounds Catalytic Enantioselective Aldol Reactions ALLYLATIONS OF C=O BONDS Introduction Reactivity of Allylmetal Reagents Boronate Additions Enantioselective Additions of Optically Active Allylic Boron Reagents Diastereoselecive Allylations with Chiral Boron Reagents Mechanistic Aspects - Lewis Acid-Promoted Addition of Allylsilanes and Allylstannanes to Aldehydes Chelation Control in the Allylation of Alpha- and Beta-Alkoxy Aldehydes Allylchromium Reagents Diastereoselective Allylations with Chiral Silanes and Stannanes Catalytic Asymmetric Allylations CHIRAL ACETALS Introduction Diastereoselective Reactions of Chiral Acetals Glycosylations Spiroketals in Natural Product Synthesis ALKENE HYDROBORATION Introduction Hydroborations with Acyclic Stereocontrol Metal-Catalyzed Hydroborations Asymmetric Hydroborations with Chiral Boranes Catalytic Asymmetric Hydroboration, Hydrosilylation, and Hydroalumination REDUCTIONS OF OLEFINS Introduction Diastereoselective Olefin Reductions by Catalytic Hydrogenation Alternative Methods for Diastereoselective Olefin Reductions Catalytic Asymmetric Olefin Hydrogenations OXIDATIONS OF OLEFINS Introduction Diastereoselective Epoxidations Enantioselective Epoxidations Asymmetric Ring-Opening of Epoxides Synthesis of Aziridines Iodolactonizations and Other Olefin Cyclizations Induced by Electrophiles Diastereoselective Dihydroxylations of Olefins Enantioselective Dihydroxylations of Olefins Enantioselective Aminohydroxylation of Olefins AMINO ACIDS Introduction Enantioselective Hydrogenations of Alpha, Beta-Didehydroamino Acids Enolate Alkylations in the Presence of Chiral Auxiliaries Alkylation of Glycine Anion Equivalents in the Presence of Chiral Phase-Transfer Catalysts Enolate Aminations Enzymatic Syntheses of Alpha-Amino Acids Catalytic Asymmetric Strecker Reactions ADDITIONS TO C=N BONDS Introduction Substrate-Controlled Diastereoselective Additions to C=N Bonds Additions to Imine Derivatives Bearing N-Bound Auxiliaries Formation of Beta-Lactams Through Staudinger Reactions Intramolecular Diastereoselective Iminium Ion Cyclizations Pictet-Spengler Reactions Catalytic Asymmetric Reductions of Imines and Imine Derivatives Catalytic Enantioselective Mannich and Mannich-Type Reactions Enantioselective Additions of Carbon Nucleophiles to C=N Bonds CONJUGATE ADDITIONS Introduction Diastereoselective Conjugate Additions Diastereoselective Conjugate Additions with Use of Chiral Auxiliari

Carreira, Erick M.

Publikationen von Carreira, Erick M.

Kvaerno, Lisbet

Publikationen von Kvaerno, Lisbet

ISBN	9783527324521
Artikelnummer	9783527324521
Medientyp	Buch
Auflage	1. Auflage
Copyrightjahr	2008
Verlag	Wiley-VCH
Umfang	XIX, 632 Seiten
Abbildungen	600 SW-Abb., 3 Tabellen
Sprache	Englisch