Modern Methods in Stereoselective Aldol Reactions

  • ID: 2254027
  • Book
  • 548 Pages
  • John Wiley and Sons Ltd
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The selective formation of bondings between molecules is one of the major challenges in organic chemistry, and the so–called aldol reaction is one of the most important for this purpose. These reactions are a highly useful tool for developing such novel substances as natural products and pharmaceuticals.

Likes its highly successful and much appreciated predecessor, "Modern Aldol Reactions", this ready reference provides 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 and substrate–controlled aldol reactions, as well as asymmetric induction in aldol additions. Furthermore, new developments in existing stereoselective aldol additions are described, such as the deployment of supersilyl groups or organocatalyzed aldol additions. All of these methodologies are presented in the context of their deployment in the total synthesis of natural products.
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Preface

STEREOSELECTIVE ACETATE ALDOL REACTIONS

Introduction

Mukaiyama Aldol Reaction

Metal Enolates

Conclusions

THE VINYLOGOUS MUKAIYAMA ALDOL REACTION IN NATURAL PRODUCT SYNTHESIS

Introduction

Aldehyde–Derived Silyl Dienol Ethers

Ester–Derived Silyl Dienol Ethers

Amide–Derived Silyl Dienol Ethers –

Vinylketene Silyl N,O–Acetals

Acyclic Acetoacetate–Derived Silyl Dienolates –

Chan′s Diene

Cyclic Acetoacetate–Derived Dienolates

Furan–Derived Silyloxy Dienes

Pyrrole–Based 2–Silyloxy Dienes

Comparison with Other Methods

ORGANOCATALYZED ALDOL REACTIONS

Introduction

Proline as Organocatalyst

Proline Derivatives as Organocatalysts

Conclusions and Outlook

SUPERSILYL PROTECTIVE GROUPS IN ALDOL REACTIONS

Introduction

Aldol Addition with Acetaldehyde–Derived Super Silyl Enol Ether

Alpha–Substituted Silyl Enol Ethers Derived from Aldehydes

Aldol Addition to Chiral Aldehydes

One–Pot Sequential Aldol Reactions

Sequential Aldol–Aldol Reactions of Acetaldehyde

Double Aldol Reactions with Alpha–Substituted Silyl Enol Ethers

Stereochemical Considerations

Aldol Reactions of Beta–Supersiloxy Methyl Ketones

Total Synthesis of Natural Products Using Supersilyl Aldol Reactions

Conclusion and Outlook

ASYMMETRIC INDUCTION IN ALDOL ADDITIONS

Introduction

Asymmetric Induction Using Chiral Ketones

Asymmetric Induction Using Chiral Aldehydes

Asymmetric Induction in the Aldol Addition of Chiral Enolates to Chiral Aldehydes

POLYPROPIONATE SYNTHESIS VIA SUBSTRATE–CONTROLLED STEREOSELECTIVE ALDOL COUPLINGS OF CHIRAL FRAGMENTS

Introduction

Principles of Stereoselective Aldol Reactions

Stereoselective Aldol Coupling of Chiral Reactants

2–Alkoxyalkyl Ethyl Ketones: 2–Desmethyl Polypropionate Equivalents

Conclusions

APPLICATION OF OXAZOLIDINETHIONES AND THIAZOLIDINETHIONES IN ALDOL ADDITIONS

Introduction

Preparation of Oxazolidinethione and Thiazolidinethione Chiral Auxiliaries

Acylation of Oxazolidinethione and Thiazolidinethione Chiral Auxiliaries

Propionate Aldol Additions

Acetate Aldol Additions

Glycolate Aldol Additions

ENZYME–CATALYZED ALDOL ADDITIONS

Introduction

Pyruvate Aldolases

N–Acetylneuraminic Acid Aldolase (NeuA)

Dihydroxyacetone Phosphate (DHAP) Aldolases

D–Fructose–6–Phosphate Aldolase and Transaldolase B Phe178Tyr: FSA–Like Aldolases

2–Deoxy–D–Ribose–5–Phosphate Aldolase (RibA or DERA)

Glycine/Alanine Aldolases

Aldol Reactions Catalyzed by Non Aldolases

Conclusions and Perspectives

Index
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Born in 1950,
Rainer Mahrwald studied chemistry at MLU Halle and subsequently joined the "Manfred von Ardenne" Research Institute in Dresden, where he led the synthetics group. He gained his doctorate under G. Wagner in Leipzig in 1979, and went on to the Institute of Organic Chemistry at the Academy of Science in Berlin, where he remained until 1990. Following a stay at the Philipps–University in Marburg, Dr. Mahrwald qualified as a lecturer at the Humboldt University Berlin, where he is now full professor.
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