Selectivities in Lewis Acid Promoted Reactions

ISBN-13: 9780792304524 / Angielski / Twarda / 1989 / 333 str.

Dieter Schinzer

Opis

The ASI workshop on "Selectivities in Lewis Acid Promoted Reactions" held in the Emmantina-Hotel in Athens-Glyfada, Greece, October 2-7, 1988 was held to bring some light into the darkness of Lewis acid induced processes. As such the workshop reflects some current trends in organic synthesis, where Lewis acids are becoming a powerful tool in many different modern reactions, e.g. Diels-Alder reactions, Ene reactions, Sakurai reactions, and in general silicon and tin chemistry. The objective of this meeting was to bring together most of the world experts in the field to discuss the major reactions promoted by Lewis acids. Organic synthesis will play a major role in this book connected with some fundamental mechanistic work on allylsilane and -tin chemistry. Both natural product synthesis and unnatural molecules are presented in the chapters. The book presents all the 15 invited lectures and the contributions of 15 posters. I am confident that the material presented in this book will stimulate the chemistry, which has been discussed on our meeting, around the world. The meeting and the book were only possible through a grant of the NATO Scientific Affairs Devision and financial support by the following companies: Kali Chemie (Hannover, W-Germany), E. Merck (Darmstadt, W-Germany), Sandoz (Basel, Switzerland), Schering (Berlin, W-Germany).

Spis treści

1: Cationic Cyclization Reactions Terminated by Pinacol Rearrangements.- 2: Control of Electrophilicity in Aliphatic Friedel Crafts Reactions.- 3: New Reactions of Ketene Silyl Acetals with Imines Promoted by Titanium (IV) and Zirconium (IV) Chlorides.- 4: Stereoselective Synthesis with Silyl Ketene Acetals and TiC14.- 5: Mechanistic Variability in the Lewis Acid-Promoted Reactions of Aldehydes with Organostannanes.- 6: Synthetic and Mechanistic Studies of Lewis Acid Mediated C-C-Bond Formation.- 7: Acylation of Alkenes and Allylsilanes.- 8: Alkylaluminum Halide Induced Reactions of Carbonyl Compounds with Unactivated Alkenes.- 9: Intramolecular Additions of Allylsilanes to Conjugated Dienones.- 10: Lewis Acid-Catalyzed Stereoselection on Carbohydrate Templates.- 11: Lewis Acid Character and Selective Reactions of Pentacoordinate Silicon Compounds.- 12: Synthesis of Clerodane Diterpenes Via Lewis Acid Catalyzed Cycload-ditions.- 13: Studies on the Mechanism of Allylmetal-Acetal Additions.- 14: Stereocontrol in Organic Synthesis Using Silicon Compounds.- 15: Chiral Lewis Acid Catalysts Or-ganoaluminum and Boron Reagent.- Access to Trifluoromethyl Indans by Cycloalkylation of ß -Aryl Trifluoromethyl-Ketones.- A Route to Aliphatic Cycles Bearing a CF3 Group.- Lewis Acid Promoted Synthesis of ß-Lactams.- Lewis Acid Promoted Rearrangements of Vinyl Actals - Basics and Applications.- Lewis Acid Promoted Sequential Multifold Michael Reactions and Application to Syntheses of Terpenoids.- Lewis Acid-Promoted Cyclization Reactions by Way of Methoxycarbonyloxonium Ion Intermediates.- Stereo-chemistry of Anthracyclinones: Chelation Versus Non-chelation Control.- Reactivity of Organosilicon Compounds towards Carbenium Ions.- Aldol Condensations of Ketones Using Chiral Boron Reagents.- Synthesis of Hydroazulenic Lactones.- Lewis-Acid Induced Reactions of Organotin Compounds.- Silica Gel-Catalyzed Cyclizations of Mixed Ketene Acetals.- Substituent-Directed Oxidation.- Lewis Acid Catalyzed Hetero Diels Alder Reactions.- Lewis Acid Catalized Double Michael Addition.