Catalytic Asymmetric Friedel-Crafts Alkylations

  • ID: 1055193
  • Book
  • 317 Pages
  • John Wiley and Sons Ltd
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This first comprehensive overview of this important synthetic reaction covers the whole spectrum of this modern and rapidly developing field. Clearly structured, the book presents all the known synthetic approaches for the construction of aromatic compounds bearing benzylic stereocenters with a defined configuration. With its representative synthetic procedures, organocatalysis and industrial applications it combines a theoretical basis with practical examples, resulting in valuable advice for beginners and experts alike.

The ultimate source for every synthetic chemistry in academia and industry.

From the contents:

∗ Michael Addition

∗ Addition to Carbonyl Compounds

∗ Allylic Alkylation

∗ Nucleophilic Substitution on Csp3 Carbons

∗ Unactivated Alkenes

∗ Asymmetric Friedel–Crafts Alkylation to Total Synthesis

∗ Industrial Applications

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GENERAL ASPECTS AND HISTORICAL BACKGROUND

Introduction

General Aspects and Historical Background

Catalytic Enantioselective FC Reactions: An Introduction

MICHAEL ADDITION

Chelating Alpha, Beta–Unsaturated Compounds

Simple Alpha, Beta–Unsaturated Substrates

Nitroalkenes

ADDITION TO CARBONYL COMPOUNDS

Aldehydes/Ketones

Imines

NUCLEOPHILIC ALLYLIC ALKYLATION AND HYDROARYLATION OF ALLENES

Introduction

Allylic Alkylations

Metallo–Catalyzed Hydroarylation of Allenes

NUCLEOPHILIC SUBSTITUTION ON CSP3 CARBON ATOMS

Ring–Opening of Epoxides

Direct Activation of Alcohols

UNACTIVATED ALKENES

Introduction

Early Studies

Rh(I)–Catalyzed Enantioselective Hydroarylation of Iminoarenes

Pt(II)–Catalyzed Enantioselective Hydroarylation of Alkenylidoles

Au(II)–Catalyzed Enantioselective Hydroarylation of Allenylindoles

Conclusions and Outlook

Experimental: Selected Procedures

CATALYTIC ASYMMETRIC FRIEDEL–CRAFTS ALKYLATIONS IN TOTAL SYNTHESIS

Introduction

Total Synthesis of Indole–Containing Compounds

Total Synthesis of Pyrrole–Containing Compounds

Friedel–Crafts Alkylation of Furan Derivatives in Total Synthesis

Friedel–Crafts Alkylation of Arenes in Total Synthesis

Asymmetric Synthesis of Natural Products Based on Diastereoselective Friedel–Crafts Reactions

INDUSTRIAL FRIEDEL–CRAFTS IN CHEMISTRY

Introduction

Green Chemistry and the Friedel–Crafts Reaction

Heterogeneous Catalysts for the Friedel–Crafts Reaction

Large Scale Hydrocarbon Processing

Conclusions and Perspectives
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"Discovered in 1877, and its versatility exploited widely since then, Friedel–Crafts alkylation is well–covered in numerous comprehensive treatises; but editors Bandini and Umani–Ronchi (both affiliated with the U. of Bologna, Italy) perceived a gap in coverage pertaining to a recent and important application in connection with the synthesis of asymmetric, optically active compounds. They have focused this volume on strategies for performing catalytic enantioselective FC alkylation (up to July 2008), with a collection of more representative diastereoselective approaches reported in one chapter. Eight contributions address general aspects and historical background, Michael Addition, addition to carbonyl compounds, nucleophilic allylic alkylation and hydroarylation of allenes, nucleophilic substitution on Csp
3 carbon atoms, unactivated alkenes, catalytic asymmetric Friedel–Crafts alkylations in total synthesis, and industrial Friedel–Crafts chemistry." (Book News Inc., February 2011)

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