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Catalytic Cascade Reactions

  • Erscheinungsdatum: 30.12.2013
  • Verlag: Wiley
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Catalytic Cascade Reactions

Demonstrates the advantages of catalytic cascade reactions for synthesizing natural products and pharmaceuticals Riding the wave of green chemistry, catalytic cascade reactions have become one of the most active research areas in organic synthesis. During a cascade reaction, just one reaction solvent, one workup procedure, and one purification step are needed, thus significantly increasing synthetic efficiency. Featuring contributions from an international team of pioneers in the field, Catalytic Cascade Reactions demonstrates the versatility and application of these reactions for synthesizing valuable compounds. The book examines both organocatalysis and transition-metal catalysis reactions, bringing readers up to date with the latest discoveries and activities in all major areas of catalytic cascade reaction research. Catalytic Cascade Reactions begins with three chapters dedicated to organocatalytic cascade reactions, exploring amines, Brønsted acids, and the application of organocatalytic cascade reactions in natural product synthesis and drug discovery. Next, the book covers: Gold-catalyzed cascade reactions Cascade reactions catalyzed by ruthenium, iron, iridium, rhodium, and copper Palladium-catalyzed cascade reactions of alkenes, alkynes, and allenes Application of transition-metal catalyzed cascade reactions in natural product synthesis and drug discovery Engineering mono- and multifunctional nanocatalysts for cascade reactions Multiple-catalyst-promoted cascade reactions
All chapters are thoroughly referenced, providing quick access to important original research findings and reviews so that readers can explore individual topics in greater depth. Drawing together and analyzing published findings scattered across the literature, this book provides a single source that encapsulates our current understanding of catalytic cascade processes. Moreover, it sets the stage for the development of new catalytic cascade reactions and their applications. PENG-FEI XU, PhD, is Director of Teaching Affairs and Professor of Chemistry at Lanzhou University and Deputy Director at the State Key Laboratory of Applied Organic Chemistry. Dr. Xu also serves as an Advisory Board member for the Chinese Chemical Society. During his scientific career, he has published more than 130 papers and received numerous honors and awards, most recently the Award of New Century Excellent Talents in Universities of China and the Thieme Journal Award. WEI WANG, PhD, is Professor of Chemistry at the University of New Mexico. Dr. Wang has published more than 160 peer-reviewed papers. He has received several awards, including The Creative Award from University of New Mexico, The Chinese-American Chemistry & Chemical Biology Professors Association Distinguished Junior Faculty Award, and The American Peptide Society Bruce W. Erickson Young Investigator Award.

Produktinformationen

    Format: ePUB
    Kopierschutz: AdobeDRM
    Seitenzahl: 440
    Erscheinungsdatum: 30.12.2013
    Sprache: Englisch
    ISBN: 9781118356647
    Verlag: Wiley
    Größe: 9659 kBytes
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Catalytic Cascade Reactions

1

AMINE-CATALYZED CASCADE REACTIONS

AIGUO SONG AND WEI WANG
1.1 Introduction 1.2 Enamine-activated cascade reactions 1.2.1 Enamine - enamine cascades 1.2.1.1 Design of enamine - enamine cascades 1.2.1.2 Examples of enamine - enamine and enamine - enamine cyclization cascades 1.2.1.3 Enamine - enamine in three-component cascades 1.2.1.4 Enamine-activated double α-functionalization 1.2.1.5 Robinson annulations 1.2.2 Enamine - iminium cascades 1.2.2.1 Design of enamine - iminium cascades 1.2.2.2 Examples of [4 + 2] reactions with enamine - activated dienes 1.2.2.3 Inverse-electron-demand [4 + 2] reactions with enamine-activated dienophiles 1.2.2.4 Enamine - iminium - enamine cascades 1.2.3 Enamine catalysis cyclization 1.2.3.1 Design of enamine-cyclization cascade reactions 1.2.3.2 Enamine-intermolecular addition cascades 1.2.3.3 Enamine-intramolecular addition cascades 1.2.3.4 Enamine-intramolecular aldol cascades 1.3 Iminium-initiated cascade reactions 1.3.1 Design of iminium - enamine cascade reactions 1.3.2 Iminium-activated Diels - Alder reactions 1.3.3 Iminium-activated sequential [4 + 2] reactions 1.3.4 Iminium-activated [3 + 2] reactions 1.3.5 Iminium-activated sequential [3 + 2] reactions 1.3.6 Iminium-activated [2 + 1] reactions 1.3.6.1 Iminium-activated cyclopropanations 1.3.6.2 Iminium-activated epoxidations 1.3.6.3 Iminium-activated aziridinations 1.3.7 Iminium-activated multicomponent reactions 1.3.8 Iminium-activated [3 + 3] reactions 1.3.8.1 Iminium-activated all-carbon-centered [3 + 3] reactions 1.3.8.2 Iminium-activated hetero-[3 + 3] reactions 1.3.9 Other iminium-activated cascade reactions 1.4 Cycle-specific catalysis cascades 1.5 Other strategies 1.6 Summary and outlook References 1.1 INTRODUCTION

Chiral amine-mediated organocatalytic cascade reactions have become a benchmark in contemporary organic synthesis, as witnessed by a number of cascade processes developed in the past decade [1]. The great success is attributed to two unique interconvertible activation modes, enamine [2] and iminium activations [3]. Enamine catalysis has been widely applied to the α-functionalizations of aldehydes and ketones. Mechanistically, dehydration between a chiral amine and the carbonyl of an aldehyde or ketone generates an intermediate, 2 , which undergoes an enantioselective α-substitution or nucleophilic addition reaction to produce respective iminium intermediate 3 or 5 ( Scheme 1.1 ). Hydrolysis affords the products and, meanwhile, releases the chiral amine catalyst.

SCHEME 1.1 Enamine-catalyzed nucleophilic substitution (a) and addition (b) reactions.

SCHEME 1.2 Iminium catalysis.

Correspondingly, iminium catalysis involves nucleophilic addition to the β-position of an iminium species 8 derived from an α,β-unsaturated aldehyde or ketone 7 with an amine catalyst ( Scheme 1.2 ).
1.2 ENAMINE-ACTIVATED CASCADE REACTIONS

We define the cascade reactions initiated by enamine catalysis in the initial step as an enamine-activated mode, although an iminium mode might be involved in the following steps. In

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