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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 chemist in academia and industry.
List of contents
GENERAL ASPECTS AND HISTORICAL BACKGROUNDIntroductionGeneral Aspects and Historical BackgroundCatalytic Enantioselective FC Reactions: An IntroductionMICHAEL ADDITIONChelating Alpha, Beta-Unsaturated CompoundsSimple Alpha, Beta-Unsaturated SubstratesNitroalkenesADDITION TO CARBONYL COMPOUNDSAldehydes/KetonesIminesNUCLEOPHILIC ALLYLIC ALKYLATION AND HYDROARYLATION OF ALLENESIntroductionAllylic AlkylationsMetallo-Catalyzed Hydroarylation of AllenesNUCLEOPHILIC SUBSTITUTION ON CSP3 CARBON ATOMSRing-Opening of EpoxidesDirect Activation of AlcoholsUNACTIVATED ALKENESIntroductionEarly StudiesRh(I)-Catalyzed Enantioselective Hydroarylation of IminoarenesPt(II)-Catalyzed Enantioselective Hydroarylation of AlkenylidolesAu(II)-Catalyzed Enantioselective Hydroarylation of AllenylindolesConclusions and OutlookExperimental: Selected ProceduresCATALYTIC ASYMMETRIC FRIEDEL-CRAFTS ALKYLATIONS IN TOTAL SYNTHESISIntroductionTotal Synthesis of Indole-Containing CompoundsTotal Synthesis of Pyrrole-Containing CompoundsFriedel-Crafts Alkylation of Furan Derivatives in Total SynthesisFriedel-Crafts Alkylation of Arenes in Total SynthesisAsymmetric Synthesis of Natural Products Based on Diastereoselective Friedel-Crafts ReactionsINDUSTRIAL FRIEDEL-CRAFTS IN CHEMISTRYIntroductionGreen Chemistry and the Friedel-Crafts ReactionHeterogeneous Catalysts for the Friedel-Crafts ReactionLarge Scale Hydrocarbon ProcessingConclusions and Perspectives
About the author
Marco Bandini received his PhD at the Alma Mater Studiurum (University of Bologna) in 2000 under the supervision of Achille Umani-Ronchi. During the Ph.D. (1999) he joined the laboratories of Micheal R. Gagné at the University of North Carolina at Chapel Hill. In 2000 he was appointed as an Assistant Professor at the Department of Chemistry "G. Ciamician", University of Bologna. In 2004 he was Marco Polo Fellow at the Center of Clean Technology, University of York, UK (Dr. Duncan J. Macquarrie. He was awarded the Co.G.I.C.O. Junior Award (2002) from the Italian Chemical Society (Organometallic Division) and Ciamician Medal (2005) in Chemistry from the Italian Chemical Society (Organic Division). His work has appeared in more then 60 publications, reviews, accounts and book chapters.
Achille Umani-Ronchi is Full Professor of Organic Chemistry at the Faculty of Sciences at the University of Bologna, Italy. In 2002 he was the recipient of the Award of the Italian Chemical Society for his contribution to the field of the organic synthesis. In 2007 he received the gold medal "Piero Pino" for the excellent results in the development of chiral organometallic catalytic systems. He is author of chapters of books and author of 180 publications on international journals. His current research work is centered on the synthesis of new chiral ligands and their applications to homogeneous and heterogeneous catalysis.
Summary
Diese Monographie enthält alle bekannten Synthesewege zum Aufbau aromatischer Verbindungen mit benzylischen Stereozentren definierter Konfiguration. Durch die gelungene Mischung von Theorie und Praxis (viele Vorschriften!) eignet sich der Band für den allgemeinen Einsteig in das Thema ebenso wie als Begleiter im Laboralltag.
Report
"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)
