Classics in Stereoselective Synthesis By Erick M. Carreira, Lisbet Kvaerno

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Classics in Stereoselective Synthesis

Erick M. Carreira, Lisbet Kvaerno
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651 pages
December 2008
Providing an excellent compilation of the most important and useful methods of modern stereoselective synthesis, this book features illustrative examples of drug and natural product syntheses, resulting in a rich source of stimulating ideas for the efficient use of asymmetric reactions in the users' own synthesis. The authors adopt a novel approach in not attempting to present this rapidly developing area in its entirety, but to distill the truly groundbreaking reactions that should be in the repertoire of every synthetic organic chemist.
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 Auxiliaries.

Enantioselective Conjugate Additions of Enolates and other Stabilized Carbon Nucleophiles.

Enantioselective Conjugate Additions of Organometallic Species.

Enantioselective Conjugate Additions of Radicals.

Enantioselective Conjugate Additions of Heteroatom Nucleophiles.

Conjugate Reductions.

Catalytic Enantioselective Stetter Reactions.

CHIRAL CARBONIONS.

Introduction.

Organolithium Reagents by Transmetalation of Organostannanes.

Carbanions by Reductive Methods.

Chiral Carbanions by Deprotonation.

Sulfoxide- and Phosphorus-Stabilized Carbanions.

Metal-Mediated Enantioselective Olefin Functionalizations.

METAL-CATALYZED ALLYLATIONS.

Introduction.

Diastereoselective Palladium-Catalyzed Allylation Reactions.

Enantioselective Palladium-Catalyzed Allylation Reactions.

Iridium-Catalyzed Enantioselective Allylation Reactions.

Copper-Catalyzed SN2' Allylation Reactions.

Enantioselective Allylation Reactions Catalyzed by Other Transition Metals.

Asymmetric Ring-Opening Reactions of Unsaturated Heterocycles.

CYCLOPROPANATIONS AND C-H INSERTION REACTIONS.

Introduction.

Diastereoselective Cyclopropanations with Carbenoids Generated from Diazoalkanes.

Enantioselective Dyclopropanations with Carbenoids Generated from Diazoalkanes.

Diastereoselective Simmons-Smith Cyclopropanations.

Enantioselective Simmons-Smith Cyclopropanations.

Alternative Classes Cyclopropanations.

Diastereoselective C-H Bonds.

SIGMATROPIC REARRANGEMENTS.

Introduction.

Claisen and Claisen-Type [3,3]-Sigmatropic Rearrangements.

Cope and Cope-Type [3,3]-Sigmatropic Rearrangements.

[2,3]-Sigmatropic Rearrangements.

Ene Reactions.

Nazarov Cyclizations.

DIELS-ALDER AND HETERO-DIELS-ALDER REACTIONS.

Introduction.

Diastereoselective Intermolecular Diels-Alder Reactions.

Diastereoselective Intramolecular Diels-Alder Reactions.

Diastereoselective Diels-Alder Reactions Using Chiral Auxiliaries.

Catalytic Enantioselective Diels-Alder Reactions.

Diastereoselective Hetero-Diels-Alder Reactions.

Enantioselective Hetero-Diels-Alder Reactions.

[3+2]- AND [2+2]-CYCLOADDITION REACTIONS.

Introduction.

Substrate-Controlled Diastereoselective [1,3]-Dipolar Cycloadditions.

Diastereoselective [1,3]-Dipolar Cycloadditions Using Chiral Auxiliaries.

Catalytic Enantioselective [1,3]-Dipolar Cycloadditions.

[3+2]-Cycloadditions with Trimethylenemethane Equivalents.

Ketene Cycloadditions.

Photochemical [2+2]-Cycloadditions.

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