Improved Synthesis and Application of Planar-chiral Nucleophilic Catalysts in Asymmetric Reactions and Copper-catalyzed Enantioselective N-H Insertion Reactions PDF Download
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Author: Elaine C. Lee Publisher: ISBN: Category : Languages : en Pages : 215
Book Description
The development of an improved synthesis of nucleophilic planar-chiral catalysts is described in Chapter 1. This route is amenable to scale-up and preparative chiral HPLC is unnecessary to resolve the racemic catalysts. Using planar-chiral catalysts, two synthetic methodology projects have been developed: Chapter 2 describes the first asymmetric synthesis of trans P-lactams, and Chapter 3 describes the asymmetric synthesis of tertiary a-chloroesters. In the chapter describing the asymmetric synthesis of trans [beta]-lactams, we present mechanistic data supporting a novel mechanism, in which the N-triflylimine, rather than the ketene, reacts with the catalyst first. In the chapter describing the asymmetric synthesis of tertiary a-chloroesters, we introduced an under-utilized commercially available chlorinating reagent (2,2,6,6-tetrachlorocyclohexanone). Finally, in chapter 4, the Cu-catalyzed asymmetric synthesis of [alpha]-aminoesters via an N-H insertion is described. We have demonstrated that carbamates such as BocNH2 and CbzNH2 are efficient coupling partners in reactions with a-diazoesters to generate highly useful Boc- or Cbz-protected a-aminoesters.
Author: Elaine C. Lee Publisher: ISBN: Category : Languages : en Pages : 215
Book Description
The development of an improved synthesis of nucleophilic planar-chiral catalysts is described in Chapter 1. This route is amenable to scale-up and preparative chiral HPLC is unnecessary to resolve the racemic catalysts. Using planar-chiral catalysts, two synthetic methodology projects have been developed: Chapter 2 describes the first asymmetric synthesis of trans P-lactams, and Chapter 3 describes the asymmetric synthesis of tertiary a-chloroesters. In the chapter describing the asymmetric synthesis of trans [beta]-lactams, we present mechanistic data supporting a novel mechanism, in which the N-triflylimine, rather than the ketene, reacts with the catalyst first. In the chapter describing the asymmetric synthesis of tertiary a-chloroesters, we introduced an under-utilized commercially available chlorinating reagent (2,2,6,6-tetrachlorocyclohexanone). Finally, in chapter 4, the Cu-catalyzed asymmetric synthesis of [alpha]-aminoesters via an N-H insertion is described. We have demonstrated that carbamates such as BocNH2 and CbzNH2 are efficient coupling partners in reactions with a-diazoesters to generate highly useful Boc- or Cbz-protected a-aminoesters.
Author: Alexandre Alexakis Publisher: John Wiley & Sons ISBN: 3527664599 Category : Science Languages : en Pages : 467
Book Description
This book reflects the increasing interest among the chemical synthetic community in the area of asymmetric copper-catalyzed reactions, and introduces readers to the latest, most significant developments in the field. The contents are organized according to reaction type and cover mechanistic and spectroscopic aspects as well as applications in the synthesis of natural products. A whole chapter is devoted to understanding how primary organometallics interact with copper to provide selective catalysts for allylic substitution and conjugate addition, both of which are treated in separate chapters. Another is devoted to the variety of substrates and experimental protocols, while an entire chapter covers the use on non-carbon nucleophiles. Other chapters deal with less-known reactions, such as carbometallation or the additions to imines and related systems, while the more established reactions cyclopropanation and aziridination as well as the use of copper (II) Lewis acids are warranted their own special chapters. Two further chapters concern the processes involved, as determined by mechanistic studies. Finally, a whole chapter is devoted to the synthetic applications. This is essential reading for researchers at academic institutions and professionals at pharmaceutical or agrochemical companies.
Author: Giorgio Della Sala Publisher: MDPI ISBN: 3036509720 Category : Science Languages : en Pages : 172
Book Description
The synthesis of enantiopure organic compounds is a key issue for several applications in pharmacology, food chemistry, agricultural chemistry, perfumery, materials science and other industrial sectors. Nowadays, asymmetric catalysis is undoubtedly the most important tool to achieve this goal. This technology, in fact, enables the production of large amounts of enantiomerically enriched compounds, employing relatively small quantities of chiral enantiopure catalysts, which is exactly what is accomplished by enzymes in nature. Since the pioneering works of Noyori, Knowles and Sharpless, which later earned them the Nobel Prize in Chemistry, asymmetric catalysis has experienced a rapid and relentless development in the last fifty years. The tremendous expansion of enantioselective transformations, the design of novel and more efficient organometallic and organic catalysts, the development of sophisticated bioreactors and cell factories, are just some of the elements responsible for such growth. However, new challenges of asymmetric catalysis are devoted to enhancing the process’s sustainability, by the introduction of recyclable and low-cost catalysts, and the use of renewable starting materials and energy source. This book provides an overview of some of these development directions and comprises a collection of review papers and a research article authored by renowned researchers actively involved in this field. The topics covered by the review papers are photoredox-catalyzed reactions of imines, asymmetric catalytic electrosynthesis, cooperative catalysis of chiral N-heterocyclic carbenes and Lewis acid, and asymmetric ring-opening reactions of epoxides catalyzed by metal–salen complexes. The research article presents a proline-catalyzed aldol reaction in water–methanol solvent mixture.
Author: Michelangelo Gruttadauria Publisher: John Wiley & Sons ISBN: 0470641363 Category : Science Languages : en Pages : 720
Book Description
This book covers advances in the methods of catalytic asymmetric synthesis and their applications. Coverage moves from new materials and technologies to homogeneous metal-free catalysts and homogeneous metal catalysts. The applications of several methodologies for the synthesis of biologically active molecules are discussed. Part I addresses recent advances in new materials and technologies such as supported catalysts, supports, self-supported catalysts, chiral ionic liquids, supercritical fluids, flow reactors and microwaves related to asymmetric catalysis. Part II covers advances and milestones in organocatalytic, enzymatic and metal-based mediated asymmetric synthesis, including applications for the synthesis of biologically active molecules. Written by leading international experts, this book consists of 16 chapters with 2000 References and illustrations of 560 schemes and figures.
Author: Takahiko Akiyama Publisher: John Wiley & Sons ISBN: 1119736390 Category : Science Languages : en Pages : 798
Book Description
Catalytic Asymmetric Synthesis Seminal text presenting detailed accounts of the most important catalytic asymmetric reactions known today This book covers the preparation of enantiomerically pure or enriched chemical compounds by use of chiral catalyst molecules. While reviewing the most important catalytic methods for asymmetric organic synthesis, this book highlights the most important and recent developments in catalytic asymmetric synthesis. Edited by two well-qualified experts, sample topics covered in the work include: Metal catalysis, organocatalysis, photoredox catalysis, enzyme catalysis C–H bond functionalization reactions Carbon–carbon bond formation reactions, carbon–halogen bond formation reactions, hydrogenations, polymerizations, flow reactions Axially chiral compounds Retaining the best of its predecessors but now thoroughly up to date with the important and recent developments in catalytic asymmetric synthesis, the 4th edition of Catalytic Asymmetric Synthesis serves as an excellent desktop reference and text for researchers and students, from upper-level undergraduates all the way to experienced professionals in industry or academia.
Author: Peter I. Dalko Publisher: John Wiley & Sons ISBN: 3527315225 Category : Science Languages : en Pages : 563
Book Description
In this reference leaders at the forefront of research provide an insight into one of the hottest topics in organic synthesis, focusing on the most important enantioselective reactions. Clearly structured, each entry begins with a concise introduction, including a mechanistic discussion of the reaction, followed by preparative guidelines for newcomers, such as carefully selected working procedures with critical notes for bench chemists, rules of thumb and tips and tricks.
Author: Uli Kazmaier Publisher: Springer Science & Business Media ISBN: 3642227481 Category : Science Languages : en Pages : 354
Book Description
Giovanni Poli, Guillaume Prestat, Frédéric Liron, Claire Kammerer-Pentier: Selectivity in Palladium Catalyzed Allylic Substitution.- Jonatan Kleimark and Per-Ola Norrby: Computational Insights into Palladium-mediated Allylic Substitution Reactions.- Ludovic Milhau, Patrick J. Guiry: Palladium-catalyzed enantioselective allylic substitution.- Wen-Bo Liu, Ji-Bao Xia, Shu-Li You: Iridium-Catalyzed Asymmetric Allylic Substitutions.- Christina Moberg: Molybdenum- and Tungsten-Catalyzed Enantioselective Allylic Substitutions.- Jean-Baptiste Langlois, Alexandre Alexakis: Copper-catalyzed enantioselective allylic substitution.- Jeanne-Marie Begouin, Johannes E. M. N. Klein, Daniel Weickmann, B. Plietker: Allylic Substitutions Catalyzed by Miscellaneous Metals.- Barry M. Trost, Matthew L. Crawley: Enantioselective Allylic Substitutions in Natural Product Synthesis.
Author: Peter I. Dalko Publisher: John Wiley & Sons ISBN: 3527658882 Category : Science Languages : en Pages : 1499
Book Description
Structured in three parts this manual recollects efficient organocatalytic transformations around clear principles that meet actual standard in asymmetric synthesis. Chapters were written by acknowledged leaders of the organocatalysis field, and are presented in a concise way. Volume 1: Privileged Catalysts gives insight to readers to the continuously increasing variety of catalysts, and the relatively complex interactions that make organocatalytic reactions selective. An appendix recollects catalyst structures with the adequate cross-references. Volume 2: Activations covers the fundamental activation types (non-covalent and covalent activations) and helps understanding the importance of physical parameters, and in particular, the role of water, that influences reactivity and selectivity. Volume 3: Reactions and Applications highlights transformations by reaction types. The final part of this volume is dedicated to application in multistep synthesis and industrial applications. Considering the ever increasing interest in the organocatalysis field, the book aims addressing to a large audience: to academic, and, industrial researchers, students and teachers who are interested in synthetic organic chemistry at advanced level. This book provides non-specialists with an introduction to the topic as well as serving as a valuable source for newcomers and researchers searching for an up-to-date and comprehensive overview of this promising area of synthetic organic chemistry.
Author: Helene Pellissier Publisher: Royal Society of Chemistry ISBN: 1782621350 Category : Science Languages : en Pages : 255
Book Description
Chiral molecules are needed for the production of many pharmaceuticals and materials, and catalytic asymmetric synthesis provides a method for the preparation of such chiral products. For the synthesis of complex molecules, such as natural products and biologically active compounds, more than one catalytic reaction may be necessary and tandem catalysis refers to the combination of catalytic reactions into one synthesis. By combing catalysts it enables a more efficient, economical and selective one pot approach for complex molecule synthesis which could not be achieved through single specific catalytic systems. The challenge is finding the right catalyst which is compatible with other catalysts but also tolerates reagents, solvent and intermediates generated during the course of the reaction. Enantioselective Multicatalysed Tandem Reactions provides an overview of recent developments in the area. The first part of the book covers asymmetric tandem reactions catalysed by multiple catalysts from the same discipline (organocatalysts, two metal and multienzyme-catalysed reactions). The second part looks at tandem reactions catalysed by multiple catalysts from different disciplines including reactions catalysed by a combination of metals and organocatalysts, reactions catalysed by a combination of metals and enzymes, and finally reactions catalysed by a combination of organocatalysts and enzymes. The book will appeal to researchers and professionals in academic and industrial laboratories interested in catalysis, biocatalysis and organic synthesis of chiral compounds.
Author: Kuiling Ding Publisher: John Wiley & Sons ISBN: 3527623027 Category : Science Languages : en Pages : 466
Book Description
In this most up-to-date handbook each chapter contains a general introduction, followed by the principles of the immobilization and, finally, applications. In this way, it covers the most important approaches currently employed for the heterogenization of chiral catalysts, including data tables, applications, reaction types and literature citations. For chemists in both academia and industry as well as those working in the fine chemical and pharmaceutical industry.
Author: Elaine C. Lee
Author: Elaine C. Lee
Author: Alexandre Alexakis
Author: Giorgio Della Sala
Author: Michelangelo Gruttadauria
Author: Takahiko Akiyama
Author: Peter I. Dalko
Author: Uli Kazmaier
Author: Peter I. Dalko
Author: Helene Pellissier
Author: Kuiling Ding