Asymmetric Synthesis Of 3 3 Disubstituted Oxindoles

Indole derivatives are the most common heterocycle compounds present in nature, for this reason, they have been referred to as 'privileged structures'. In fact, many approved drugs — and natural products — belong to this family. Among indole derivatives, oxindoles have a structural complexity, which have stimulated generations of synthetic chemists to design strategies for assembling these structures, and their enantioselective synthesis is still growing.This book proposes to describe the known enantioselective syntheses of oxindole derivatives. It is divided in six chapters each referring to a specific class of asymmetric oxindole derivatives. After the introduction, Chapter 2 describes all-carbon spirooxindoles; Chapter 3, open chain 3,3-dialkyloxindoles; Chapter 4, 3-substituted-3-aminooxindoles; Chapter 5, 3-substituted-3-hydroxyoxindoles; Chapter 6, 3-hetero-3-substituted oxindoles. It will be a useful tool for synthetic chemists, who assemble total synthesis of natural products, as well as for drug discovery chemists either in academic or in industry R&S laboratories.

"Indole derivatives are the most common heterocycle compounds present in nature, for this reason, they have been referred to as "privileged structures". In fact, many approved drugs - and natural products - belong to this family. Among indole derivatives, oxindoles have a structural complexity, which have stimulated generations of synthetic chemists to design strategies for assembling these structures, and their enantioselective synthesis is still growing. This book proposes to describe the known enantioselective syntheses of oxindole derivatives. It is divided in six chapters each referring to a specific class of asymmetric oxindole derivatives. After the introduction, Chapter 2 describes all-carbon spirooxindoles; Chapter 3, open chain 3,3-dialkyloxindoles; Chapter 4, 3-substituted-3-aminooxindoles; Chapter 5, 3-substituted-3-hydroxyoxindoles; Chapter 6, 3-hetero-3-substituted oxindoles. It will be a useful tool for synthetic chemists, who assemble total synthesis of natural products, as well as for drug discovery chemists either in academic or in industry R&S laboratories."--

Natural products in the plant and animal kingdom offer a huge diversity of chemical structures that are the result of biosynthetic processes that have been modulated over the millennia through genetic effects. With the rapid developments in spectroscopic techniques and accompanying advances in high-throughput screening techniques, it has become possible to isolate and then determine the structures and biological activity of natural products rapidly, thus opening up exciting new opportunities in the field of new drug development to the pharmaceutical industry. The series also covers the synthesis or testing and recording of the medicinal properties of natural products. Describes the chemistry of bioactive natural products Contains contributions by leading authorities in the field A valuable resource for natural products and medicinal chemistry

Functional diversity and molecular architecture in biologically active oxindoles. Transition metal-catalyzed intramolecular Heck reactions and amide alpha-arylations. Asymmetric rearrangements of O-carbonylated oxindoles and related processes. Amination, hydroxylation, and halogenation reactions of 3-substituted oxindoles. Conjugate addition and alkylation reactions of 3-substituted oxindoles. Asymmetric aldol and Mannich reactions of isatins. Michael additions to isatin-derived electron-deficient alkynes. Nucleophilic substitution reactions of functionalized 3-substituted oxindoles. Enantioselective construction of spirooxindoles by cycloaddition, annulation, and cascade cyclization reactions of methyleneindolinone derivatives. The 3,3-disubstituted-2-oxindole moiety is present in many chiral alkaloids that exhibit interesting biological activities. The enantioselective synthesis of chiral oxindole derivatives has been mainly achieved by asymmetric catalytic methods. In this review we highlight the most important catalytic methods relevant to the synthesis of chiral, non-spirocyclic 3,3-disubstituted oxindoles.

The series Topics in Heterocyclic Chemistry presents critical reviews on present and future trends in the research of heterocyclic compounds. Overall the scope is to cover topics dealing with all areas within heterocyclic chemistry, both experimental and theoretical, of interest to the general heterocyclic chemistry community. The series consists of topic related volumes edited by renowned editors with contributions of experts in the field. All chapters from Topics in Heterocyclic Chemistry are published Online First with an individual DOI. In references, Topics in Heterocyclic Chemistry is abbreviated as Top Heterocycl Chem and cited as a journal.

Asymmetric synthesis has become a major aspect of modern organic chemistry. The stereochemical properties of an organic compound are often essential to its bioactivity, and the need for stereochemically pure pharmaceutical products is a key example of the importance of stereochemical control in organic synthesis. However, achieving high levels of stereoselectivity in the synthesis of complex natural products represents a considerable intellectual and practical challenge for chemists. Written from a synthetic organic chemistry perspective, this text provides a practical overview of the field, illustrating a wide range of transformations that can be achieved. The book captures the latest advances in asymmetric catalysis with emphasis placed on non-enzymatic methods. Topics covered include: Reduction of alkenes, ketones and imines Nucleophilic addition to carbonyl compounds Catalytic carbon-carbon bond forming reactions Catalytic reactions involving metal carbenoids Conjugate addition reactions Catalysis in Asymmetric Synthesis bridges the gap between undergraduate and advanced level textbooks and provides a convenient point of entry to the primary literature for the experienced synthetic organic chemist.

This book introduces multi-catalyst systems by describing their mechanism and advantages in asymmetric catalysis. • Helps organic chemists perform more efficient catalysis with step-by-step methods • Overviews new concepts and progress for greener and economic catalytic reactions • Covers topics of interest in asymmetric catalysis including bifunctional catalysis, cooperative catalysis, multimetallic catalysis, and novel tandem reactions • Has applications for pharmaceuticals, agrochemicals, materials, and flavour and fragrance

Advances in Heterocyclic Chemistry is the definitive series in the field - one of great importance to organic chemists, polymer chemists, and many biological scientists. Because biology and organic chemistry increasingly intersect, the associated nomenclature also is being used more frequently in explanations. Written by established authorities in the field from around the world, this comprehensive review combines descriptive synthetic chemistry and mechanistic insight to yield an understanding of how chemistry drives the preparation and useful properties of heterocyclic compounds. Considered the definitive serial in the field of heterocyclic chemistry Serves as the go-to reference for organic chemists, polymer chemists and many biological scientists Provides the latest comprehensive reviews written by established authorities in the field Combines descriptive synthetic chemistry and mechanistic insight to enhance understanding of how chemistry drives the preparation and useful properties of heterocyclic compounds