Classics in Stereoselective Synthesis

  • ID: 683696
  • Book
  • 651 Pages
  • John Wiley and Sons Ltd
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This book provides a noteworthy compilation oft he groundbreaking methods of stereoselective synthesis, belonging to the repertoire of every modern practitioner of synthetic organic chemistry. The general principles underlying these processes are highlighted as they form the basis for the rapid and continuing developments in the field. The work also features illustrative examples of drug and natural product synthesis, resulting in a rich source of stimulating ideas for the efficient use of asymmetric reactions in the construction of sterochemically complex structures.

From the contents:

∗Macrocyclic stereocontrol

∗Carbonyl addition reactions

∗Alpha–Functionalization of enolates

∗Aldol and allylation reactions

∗Chiral acetals

∗Alkene hydroboration, reduction, and oxidation

∗Additions to C=N bonds and synthesis of amino acids

∗Conjugate additions

∗Chiral carbonions

∗Metal–catalyzed allylations

∗Cyclopropanations and CH–insertion reactions

∗Sigmatropic rearrangements

∗Diels–Alder and hetero–Diels–Alder reactions

∗[3+2]– and [2+2]–cycloaddition reactions

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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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Erick M. Carreira
Lisbet Kvaerno
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