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Catalytic Asymmetric Friedel-Crafts Alkylations

Catalytic Asymmetric Friedel-Crafts Alkylations

Marco Bandini (Editor), Achille Umani-Ronchi (Editor), George A. Olah (Foreword by)

ISBN: 978-3-527-62698-4

Jun 2009

317 pages

$187.99

Description

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 chemist in academia and industry.
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
"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)