Asymmetric Organocatalysis in Natural Product Syntheses

ISBN-13: 9783709111628 / Angielski / Twarda / 2012 / 197 str.

Mario Waser

Opis

This book provides an illustrative overview of successful and widely used applications of organocatalysis in the field of natural product synthesis. The main focus is on organocatalytic key-steps for each (multi-step) synthesis described.

Spis treści

1 Introduction.- 2 Enamine Catalysis.- Aldol Reactions.- Mannich Reactions.- a-Heterofunctionalizations.- Conjugate Additions.- Dienamine Catalysis.- Combined Enamine-Catalyzed Approaches and Cascade Reactions.- Synopsis.- 3 Iminium Catalysis.- Pericyclic Reactions.- Conjugate Additions.- Iminium-Catalyzed Organocascade Reactions.- Synopsis.- 4 Combined Iminium-Enamine Catalyzed Approaches.- Cascade Reactions Using a Single Organocatalyst.- Organocascade Catalysis Using a Combination of Different Catalysts.- Synopsis.- 5 Singly Occupied Molecular Orbital (SOMO) Catalysis.- Friedel-Crafts Reactions.- Epoxide Formation.- Synopsis.- 6 Asymmetric Phase-Transfer Catalysis.- Asymmetric a-Alkylations.- Phase-Transfer Catalyzed Michael Additions.- Alkylative Dearomatization-Annulation Reaction.- Synopsis.- 7 Chiral Brønsted Acids and Hydrogen Bonding Donors.- Chiral Phosphoric Acids.- Chiral Diols.- Chiral (Thio)-Ureas.- Bifunctional Brønsted Acid-Base Active (Thio)-Ureas.- Synopsis.- 8 Chiral Brønsted and Lewis Bases.- Cinchona Alkaloids.- Phosphine Catalysis.- Carbene Catalysis.- Synopsis.- 9 Asymmetric Oxidations and Reductions.- Organocatalytic Oxidations.- Organocatalytic Reductions.- Synopsis.- 10 Conclusions.

O autorze

Mario Waser was born in Steyr, Austria in 1977. After studying chemistry at the Johannes Kepler University (JKU) Linz, Austria, he finished his Ph.D. thesis in 2005 in the group of Prof. Dr. Heinz Falk, working on the synthesis of second-generation hypericin-based photosensitizers. After a postdoctoral stay in the group of Prof. Dr. Alois Fürstner at the Max-Planck Institut für Kohlenforschung (Mülheim, Germany), investigating the first total syntheses of iejimalide B and iejimalide A, he spent two years as a research and development chemist for DSM Linz. Since the summer of 2009 he has held the position of Assistant Professor at JKU Linz, where he is currently working on his habilitation. Dr. Waser’s main research interests are focused in the field of synthetic organic chemistry with a special emphasis on ammonium ylide-mediated (dia)-stereoselective reactions and the design of new tartaric acid-derived organocatalysts.

Blurb

This book provides the reader with an illustrative overview concerning successful and widely used applications of organocatalysis in the field of natural product synthesis. The main focus will be on organocatalytic key-steps for each (multi-step) synthesis described, whereas other often particularly innovative transformations will be omitted, as this would be beyond the scope of this volume.