Recent advances in organocatalytic cascade reactions for enantioselective synthesis of chiral spirolactone skeletons

Recent advances in organocatalytic cascade reactions for enantioselective synthesis of chiral spirolactone skeletons PDF Author: Jun Yang
Publisher: OAE Publishing Inc.
ISBN:
Category : Science
Languages : en
Pages : 54

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Book Description
Chiral spirolactones, including spiropropyllactones, spirobutyrolactones, and spirovalerolactones, are important heterocyclic frameworks that attracted the attention of organic and medicinal chemists because these motifs constitute the core structure of several natural products and bioactive molecules. The absolute configuration and the substituents on the fully substituted spirocyclic stereocenter of the lactone can potentially enhance specificity for ligand-protein binding and enhance bioavailability, potency, and metabolic stability. So, intensive attention from chemists has been paid to the synthetic methods leading to such prominent structural motifs. The synthetic methods can be divided into two main classes. The first approach takes advantage of the presence of the existing lactone structure and focuses on its functionalization. The second approach is the lactone framework constructed from various precursors in a direct spirolactonization reaction. In this review, for convenience in reading, the recent advances in the synthesis of spirolactones are summarized and discussed according to the two major organocatalytic asymmetric synthetic routes: (i) using the lactone-related frameworks as building blocks; and (ii) direct spirolactonization reaction using various reagents. This review also describes both the mechanisms and related transformations, and gives some insights into challenging issues in this research field, which will enlighten the future development of this field.

Recent advances in organocatalytic cascade reactions for enantioselective synthesis of chiral spirolactone skeletons

Recent advances in organocatalytic cascade reactions for enantioselective synthesis of chiral spirolactone skeletons PDF Author: Jun Yang
Publisher: OAE Publishing Inc.
ISBN:
Category : Science
Languages : en
Pages : 54

Get Book Here

Book Description
Chiral spirolactones, including spiropropyllactones, spirobutyrolactones, and spirovalerolactones, are important heterocyclic frameworks that attracted the attention of organic and medicinal chemists because these motifs constitute the core structure of several natural products and bioactive molecules. The absolute configuration and the substituents on the fully substituted spirocyclic stereocenter of the lactone can potentially enhance specificity for ligand-protein binding and enhance bioavailability, potency, and metabolic stability. So, intensive attention from chemists has been paid to the synthetic methods leading to such prominent structural motifs. The synthetic methods can be divided into two main classes. The first approach takes advantage of the presence of the existing lactone structure and focuses on its functionalization. The second approach is the lactone framework constructed from various precursors in a direct spirolactonization reaction. In this review, for convenience in reading, the recent advances in the synthesis of spirolactones are summarized and discussed according to the two major organocatalytic asymmetric synthetic routes: (i) using the lactone-related frameworks as building blocks; and (ii) direct spirolactonization reaction using various reagents. This review also describes both the mechanisms and related transformations, and gives some insights into challenging issues in this research field, which will enlighten the future development of this field.

Organocatalytic Enantioselective Conjugate Addition Reactions

Organocatalytic Enantioselective Conjugate Addition Reactions PDF Author: Jose L Vicario
Publisher: Royal Society of Chemistry
ISBN: 1849732183
Category : Science
Languages : en
Pages : 365

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Book Description
This book, unique in its field, is a comprehensive description of all the methodologies reported for carrying out conjugate addition reactions in a stereoselective way, using small chiral organic molecules as catalysts (organocatalysts). In the last 3-4 years, this has been a rapidly growing field in organic chemistry, and many papers have appeared reporting excellent protocols for carrying out these highly efficient transformations that compete well with other classical approaches using transition metal catalysts. A particularly attractive feature of this transformation relies upon the fact that the conjugate addition (Michael and Hetero-Michael reactions) is an extraordinarily effective means to initiate cascade processes which result in the formation of complex molecules from very small and simple starting blocks. The book, written by noted experts, covers all recent advances in this hot topic, and provides a good state-of-the-art review for organic chemists working in this field and all those who wish to start projects in this area.

Enantioselective Organocatalysis

Enantioselective Organocatalysis PDF Author: Peter I. Dalko
Publisher: John Wiley & Sons
ISBN: 3527610952
Category : Science
Languages : en
Pages : 559

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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.

The Development Of New Organocatalysts and New Organocatalytic Cascade Reactions

The Development Of New Organocatalysts and New Organocatalytic Cascade Reactions PDF Author: Patrick Gordon McGarraugh
Publisher:
ISBN:
Category :
Languages : en
Pages : 994

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Book Description
Organocatalysis is the use of small organic molecules to catalyze chemical reactions. They are generally cheaper, less toxic, and easier to handle on a laboratory and industrial scale than more traditional metal-based catalysts. This dissertation discusses the development of new organocatalysts and organocatalytic methods for the asymmetric synthesis of useful small molecules. The research conducted has specifically focused on the use of chiral diarylprolinol silyl ether organocatlysts and their ability to catalyze a variety of useful cascade reactions through iminium and enamine catalysis. Cascade reactions are useful in that a great deal of molecular complexity may be generated in a one-pot process using simple, readily available building blocks. Herein, is provided a comprehensive background on the use of diarylprolinol silyl ethers in the catalysis of iminium-initiated cascade reactions. The research conducted has focused on three main topics: 1.) The development of a novel class of bifunctional bissulfonamide organocatalysts for the asymmetric conjugate addition of dicarbonyls to nitroolefins. 2.) The use of diarylprolinol silyl ether organocatalysts to catalyze a novel Michael-Michael cascade reaction which generates fused carbocycles. 3.) The discovery and development of a novel organocascade kinetic resolution reaction using diarylprolinol silyl ether organocatalysts, which can be used for the synthesis of chiral 2,6-disubstituted tetrahydropyrans and chiral 2,5-disubstituted tetrahydrofurans.

Catalytic Asymmetric Synthesis

Catalytic Asymmetric Synthesis PDF Author: Takahiko Akiyama
Publisher: John Wiley & Sons
ISBN: 1119736412
Category : Science
Languages : en
Pages : 798

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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.

Isocyanide-based Multicomponent Reactions

Isocyanide-based Multicomponent Reactions PDF Author: Jonathan G. Rudick
Publisher: Frontiers Media SA
ISBN: 2889634841
Category :
Languages : en
Pages : 100

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Book Description
This eBook is a collection of articles from a Frontiers Research Topic. Frontiers Research Topics are very popular trademarks of the Frontiers Journals Series: they are collections of at least ten articles, all centered on a particular subject. With their unique mix of varied contributions from Original Research to Review Articles, Frontiers Research Topics unify the most influential researchers, the latest key findings and historical advances in a hot research area! Find out more on how to host your own Frontiers Research Topic or contribute to one as an author by contacting the Frontiers Editorial Office: frontiersin.org/about/contact.

N-Heterocyclic Carbenes in Organocatalysis

N-Heterocyclic Carbenes in Organocatalysis PDF Author: Akkattu T. Biju
Publisher: John Wiley & Sons
ISBN: 3527809058
Category : Science
Languages : en
Pages : 407

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Book Description
Summarizing the emerging field of N-heterocyclic carbenes used in organocatalysis, this is an excellent overview of the synthesis and applications of NHCs focusing on carbon-carbon and carbon-heteroatom bond formation. Alongside comprehensive coverage of the synthesis, characteristics and applications, this handbook and ready reference also includes chapters on NHCs for polymerization reactions and natural product synthesis.

Cycloaddition Reactions in Organic Synthesis

Cycloaddition Reactions in Organic Synthesis PDF Author: W. Carruthers
Publisher: Elsevier
ISBN: 008091232X
Category : Science
Languages : en
Pages : 382

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Book Description
Demonstrates the wide scope of cycloaddition reactions, including the Diels-Alder reaction, the ene reaction, 1,3-dipolar cycloadditions and [2+2] cycloadditions in organic synthesis. The author, a leading exponent of the subject, illustrates the ways in which they can be employed in the synthesis of a wide range of carbocyclic and heterocyclic compounds, including a variety of natural products of various types. Special attention is given to intramolecular reactions, which often provide a rapid and efficient route to polycyclic compounds, and to the stereochemistry of the reactions, including recent and developing work on enantioselective synthesis.

Hydroformylation for Organic Synthesis

Hydroformylation for Organic Synthesis PDF Author: Maurizio Taddei
Publisher: Springer
ISBN: 3642450598
Category : Science
Languages : en
Pages : 233

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Book Description
The Role of Metals and Ligands in Organic Hydroformylation, by Luca Gonsalvi, Antonella Guerriero, Eric Monflier, Frédéric Hapiot, Maurizio Peruzzini. Hydroformylation in Aqueous Biphasic Media Assisted by Molecular Receptors, by Frédéric Hapiot, Hervé Bricout, Sébastien Tilloy, Eric Monflier. Asymmetric Hydroformylation, by Bernabé F. Perandones, Cyril Godard, Carmen Claver. Domino Reactions Triggered by Hydroformylation, by Elena Petricci, Elena Cini. Rhodium-Catalyzed Hydroformylation in Fused Azapolycycles Synthesis, by Roberta Settambolo. Hydroformylation in Natural Product Synthesis, by Roderick W. Bates, Sivarajan Kasinathan.

Organophosphorus Chemistry

Organophosphorus Chemistry PDF Author: David W Allen
Publisher: Royal Society of Chemistry
ISBN: 1788018648
Category : Science
Languages : en
Pages : 410

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Book Description
This annual review of the literature presents a comprehensive and critical survey of the vast field of study involving organophosphorus compounds, from phosphines and related P-C bonded compounds to phosphorus acids, phosphine chalcogenides and nucleotides. The Editors have added to the content with a timely chapter on the recent developments in green synthetic approaches in organophosphorus chemistry to reflect current interests in the area. With an emphasis on interdisciplinary content, this book is aimed at the worldwide organic chemistry and engineering research communities.