Synthesis Of Planar Chiral Ferrocenyl Motifs And Their Application In Asymmetric Catalysis And Medicinal Chemistry

This book meets the long-felt need for a reference on ferrocenes with the focus on catalysis. It provides a thorough overview of the synthesis and characterization of different types of chiral ferrocene ligands, their application to various catalytic asymmetric reactions, and versatile chiral materials as well as drug intermediates synthesized from them. Written by the "who's who" of ferrocene catalysis, this is a guide to the design of new ferrocene ligands and synthesis of chiral synthetic intermediates, and will thus be useful for organic, catalytic and synthetic chemists working in academia, industrial research or process development.

With applications ranging from asymmetric catalysis to magnetic materials, ferrocene is one of the most versatile building blocks in synthesis. This book captures the multidisciplinary nature of ferrocene research, including topics such as ferrocene-containing polymers, ferrocene-containing thermotropic liquid crystals, chiral ferrocene derivatives, and ferrocene-containing charge-transfer materials. In addition, the reader will find * valuable information for planning syntheses * over 70 tables, making relevant data available at a glance * carefully selected references, providing an easy access to the primary literature Up-to-date, and written by leading international experts in the field, among them R. Deschenaux, C. D. Hall, Y. Butsugan, and R. Herrmann, this book is a welcome source of in-depth information for graduate students and professionals in organic, organometallic, and polymer chemistry, as well as in materials science.

This thesis discusses the use of asymmetric organic catalysis for the direct enantioselective synthesis of complex chiral molecules, and by addressing the many aspects of both vinylogy and atropisomerism, it appeals to researchers and scholars interested in both areas. Organocatalysis is a relatively modern and “hot” topic in the chemical community; it is constantly expanding and its use has been extended to interesting areas like vinylogous reactivity and atropisomerism. Vinylogous systems are very important for their synthetic applications but also pose a number of challenges, the most notable of which are their reduced reactivity and the reduced stereocontrol at these positions. On the other hand, atropisomeric systems are even more important because of the huge potential they have as drugs, ligands and catalysts. Chemists have only recently “recognized” the importance of these two areas and are focusing their efforts on studying them and the challenges they pose. This thesis offers an extensive introduction on the general aspects of chirality and organocatalysis and an equally extensive experimental section that allow nonexperts to understand the discussion section and reproduce the experiments.

Chiral Building Blocks in Asymmetric Synthesis A comprehensive introduction to the important classes of chiral building blocks Chirality — the asymmetric quality found in certain chemical compounds — plays an essential role in our world: chiral compounds can be found in biology, pharmaceutical compounds, agrochemicals, and fragrances. The stereoselective preparation of these complex molecular constructions constitutes a challenge. To this end, modern asymmetric synthesis utilizes a variety of valuable and efficient reagents employed as chiral auxiliaries, metal complexes and organocatalysts in stereoselective catalysis, and enantiopure reactants termed as chiral building blocks. In Chiral Building Blocks in Asymmetric Synthesis, the achievements in the fields of preparation of and applications of chiral blocks are presented. In doing so, the book comprehensively discusses the important classes of these reactants as the key for the asymmetric synthesis of chiral molecules. As such, it is an indispensable resource about synthetic methods, as well as possible modifications and transformations of important classes of chiral compounds. It also highlights the importance of their use as reactants and auxiliaries in the preparation of more sophisticated molecules or supramolecular systems. In Chiral Building Blocks in Asymmetric Synthesis readers will also find: Organization according to the most important compound classes — e.g. amino acids, BINOL and its derivatives, terpenes, and others — with an emphasis on synthesis and application A focus on the use of chiral building blocks for the preparation of bioactive compounds and supramolecular assemblies Chiral Building Blocks in Asymmetric Synthesis is a useful reference for organic chemists, catalytic chemists, chemists in industry, medicinal chemists, pharmaceutical chemists, and the libraries that support them.

Today, arylation methods are belonging to the most important reaction types in organic synthesis. Lutz Ackermann, a young and ambitious professor has gathered a number of top international authors to present the first comprehensive book on the topic. Starting from a historical review, the book covers hot topics like Palladium-catalyzed arylation of N-H and alpha-C-H-acidic Bonds, Copper-catalyzed arylation of N-H and O-H Bonds, direct arylation reactions, carbanion aromatic synthesis, arylation reactions of alkenes, alkynes and much more. This compact source of high quality information is indispensable to synthetic chemists and those working in the pharmaceutical and chemical industry.

In Part I, nickel-catalyzed asymmetric carbon-carbon bond-forming reactions are described. A nickel/Pybox system effectively catalyzes regio- and enantioselective cross-couplings between racemic secondary allylic chlorides and readily available alkylzinc halides. This method is applied to generate two stereo centers in a formal total synthesis of fluvirucinine A1. In Part II, the use of planar-chiral compounds as ligands or catalysts in organic synthesis is described. A C2-symmetric planar-chiral bipyridine is an efficient ligand for copper-catalyzed asymmetric [4+1]-cycloadditions between enones and diazoacetates to form 2,3-dihydrofurans. The highly substituted dihydrofurans are not only obtained in good stereoselectivity but also readily converted to other useful molecules. This method is applied to the first catalytic enantioselective synthesis of a deoxy-C-nucleoside. The synthesis of new C2-symmetric planar-chiral catalysts is described. The diastereoslective functionalization of ferrocene using a chiral directing group enables the formation of a number of amines in enantiopure form. These catalysts are tested as several asymmetric catalysts.