Novel Strategies for the Synthesis and Cycloisomerization Reactions of Functionalized Allenes PDF Download
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Author: Gürkan Eray Akpınar
Publisher:
ISBN:
Category :
Languages : en
Pages :
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Book Description
Author: Gürkan Eray Akpınar
Publisher:
ISBN:
Category :
Languages : en
Pages :
Get Book Here
Book Description
Author:
Publisher:
ISBN:
Category :
Languages : en
Pages :
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Book Description
Allenes are very important chemical reagents in organic synthesis. Due to their high reactivity, they have been extensively used to carry out a variety of unique and effective chemical transformations including but not limited to ionic and free radical additions and transition metal catalyzed cyclizations. As the chemistry of this group of compounds is explored further and their applications expanded there is a need to develop alternative and cost effective methods for their synthesis. Our approach involves the synthesis of allenes from oxa-bicyclo-alkan-2-ones by methyllithium induced Eschenmoser fragmentation of the bicyclotosylhydrazone derivatives.
Author: Tony Wiederhold
Publisher:
ISBN:
Category :
Languages : en
Pages : 238
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Author: Michael Harmata
Publisher: Elsevier
ISBN: 0080556027
Category : Science
Languages : en
Pages : 537
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A classic in the area of organic synthesis, Strategies and Tactics in Organic Synthesis provides a forum for investigators to discuss their approach to the science and art of organic. Rather than a simple presentation of data or a second-hand analysis, we are given stories that vividly demonstrate the power of the human endeavour known as organic synthesis and the creativity and tenacity of its practitioners. First hand accounts of each project tell of the excitement of conception, the frustration of failure and the joy experienced when either rational thought and/or good fortune give rise to successful completion of a project. In this book we learn how synthesis is really done and are educated, challenged and inspired by these stories, which portray the idea that triumphs do not come without challenges. We also learn that we can meet challenges to further advance the science and art of organic synthesis, driving it forward to meet the demands of society, in discovering new reactions, creating new designs and building molecules with atom and step economies that provide solutions through function to create a better world.* Presents state-of-the-art developments in organic synthesis * Provides insight and offers new perspective to problem-solving * Written by leading experts in the field
Author: Robert Kalish
Publisher:
ISBN:
Category : Allene
Languages : en
Pages : 274
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Author: Herbert F. Schuster
Publisher: Wiley-Interscience
ISBN:
Category : Science
Languages : en
Pages : 396
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Illustrates alternate and frequently superior methods for synthesizing complex molecules, focusing on those allenes that form either carbon-carbon bonds, or carbon-heteroatom bonds. The material is extremely useful in keeping the organic chemist up-to-date on the latest methods for their preparation.
Author:
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Category :
Languages : en
Pages : 0
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Many biologically active molecules contain three or more contiguous heteroatom stereocenters (`triads'), but rapid installation of these motifs can be a strategic challenge when one must consider the abundance of possible patterns and stereochemical configurations. In order to accomplish the synthesis of these motifs, we have focused our efforts to develop methods that allow rapid construction of heteroatom stereotriads from allenes. This was accomplished with bicylic methylene aziridine intermediates that are synthesized by an intramolecular metal catalyzed nitrene transfer reaction on an allene. In the first portion of this dissertation, the methylene aziridine's fate will follow an `electrophile then nucleophile' approach. In chapter 2, this strategy yields N,N,X spiroaminals from intermediate diazaspiro[2.2]pentane intermediates. Chapter 3 will focus on a unique rearrangement of these spiroaminals to yield N,O,N stereotriads. Chapter 4 will center on the synthesis of O,O,N stereotriads via dihydroxylation of the methylene aziridine. In our efforts to synthesize methylene aziridines, we found it increasingly difficult to control the outcome of nitrene transfer reactions. In the second portion of this thesis, Chapter 6, 7, and 8 will detail our efforts to control the selectivity of amination. Chapter 6 examines a method to control for C-H aminated allenes through substrate dependence by Rh catalyzed C-H amination of propargyl C-H bonds which can then be transformed into the desired allene. Chapter 7 will introduce a Ag nitrene transfer catalyst system that is capable of selective allene aziridination. The work in Chapter 8 then evolves this system by demonstrating that this Ag catalyst can be modified by adjustments in ligand stoichiometry. This simple alteration to the system reveals a catalyst that is capable of favoring the C-H insertion products over aziridine products. The consequence of these results gave rise to we now refer to as "dynamic catalysis". The last chapter of this thesis will delve into our attempts to synthesize the natural product jogyamycin with our allene fuctionalization protocols. These attempts demonstrate that our allene functionalization methods are viable for generating rapid and densely functionalized aminocyclopentitols, which will provide useful synthetically diversified variants of the jogyamycin core for biological evaluation.
Author: Joseph Ryan Cusick
Publisher:
ISBN:
Category : Allene
Languages : en
Pages : 398
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Book Description
Disclosed are studies on the structure and reactivity of allenes and spirodiepoxides (SDEs) and their application to synthesis. A novel ruthenium promoted cycloisomerization of [gamma]-enallenes to cyclopentenes was discovered. The effects of solvent, oxidant, and substrate structure on the stereoselectivity of SDE formation from 1,3-disubstituted and trisubstituted allenes were evaluated. A computational model was advanced for the rationalization of observed selectivity in such formations. The known acid instability of SDEs was exploited to effect a designed rearrangement of [beta]-silyl SDE to an [alpha]-hydroxy enone. Silyl-substituted SDEs were utilized to give carbinol substituted heterocycles with excellent ee, [alpha]-hydroxy enones, as well as [alpha], [beta]-dihydroxy olefins. A silyl-SDE approach was used to accomplish a short and efficient total synthesis of the natural product, epi-citreodiol. A de novo synthesis of the anticancer natural product jaspine B was also achieved using a SDE-based approach.
Author: LeGrande M. Slaughter
Publisher: Springer
ISBN: 3319137220
Category : Science
Languages : en
Pages : 292
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Book Description
The series Topics in Current Chemistry presents critical reviews of the present and future trends in modern chemical research. The scope of coverage is all areas of chemical science including the interfaces with related disciplines such as biology, medicine and materials science. The goal of each thematic volume is to give the non-specialist reader, whether in academia or industry, a comprehensive insight into an area where new research is emerging which is of interest to a larger scientific audience. Each review within the volume critically surveys one aspect of that topic and places it within the context of the volume as a whole. The most significant developments of the last 5 to 10 years are presented using selected examples to illustrate the principles discussed. The coverage is not intended to be an exhaustive summary of the field or include large quantities of data, but should rather be conceptual, concentrating on the methodological thinking that will allow the non-specialist reader to understand the information presented. Contributions also offer an outlook on potential future developments in the field. Review articles for the individual volumes are invited by the volume editors. Readership: research chemists at universities or in industry, graduate students.
Author: Daniel Sole
Publisher: Academic Press
ISBN: 0128116528
Category : Science
Languages : en
Pages : 368
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Book Description
Advances in Transition-Metal Mediated Heterocyclic Synthesis provides an overview of recent catalytic reactions involving transition metals to produce heterocyclic compounds. The book is organized according to the type of transformation used to achieve the synthesis of the heterocyclic systems (mainly aza- and oxa-heterocycles). As such, it covers recent applications on the synthesis of heterocycles, also describing the details of the novel transformations in a didactic manner to motivate readers in search of new catalytic processes. The editors have included state-of-the-art strategies, including transition-metal reactions involving unsaturated systems (reactions of allenes, new gold(I)-catalyzed reactions, and Prins reaction). Chapters highlight the versatility of organopalladium chemistry dealing with carbonylative transformations, C-H activation reactions, coupling processes, and the control of the ambiphilic character of organopalladium species. Finally, the book discusses new reactions leading to heterocycles based on C-H activation processes catalyzed by other metals (Rh, Ru, Co). Written by an outstanding team of authors who are leading experts in organometallic chemistry and organic synthesis, this book is a valuable resource not only for chemists mainly focused on synthesis, but also for those interested in reaction mechanisms involving transition metals. - Helpfully organized by transformation type to stimulate the search for new synthetic processes - Completely illustrated and written by global experts - Includes thoughtfully selected strategies chosen by the editors to exemplify the state-of-the-art of the subject, including transition-metal reactions involving unsaturated systems, organopalladium chemistry, and metal-catalyzed C-H activation
