A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions

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摘要：

Approaches to research in organic chemistry are as numerous as the reactions they describe. In this account, we describe our reactivity-based approach. Using our work in the area of gold catalysis as a background, we discuss how a focus on reaction mechanism and reactivity paradigms can lead to the rapid discovery of new synthetic tools. 1 Introduction 2 Addition Reactions 2.1 Conia-Ene Reaction 2.2 Asymmetric Hydroamination 2.3 Chiral Counteranions 2.4 Exploiting Basic Counteranions 2.5 Ring Expansion Reactions 2.6 Intramolecular Carboalkoxylation 2.7 Rationalizing the π-Acidity of Cationic Gold(I) Complexes 3 Reactions Involving Carbenoid Intermediates 3.1 1,5-Enyne Cycloisomerization 3.2 Intramolecular Addition of Dipolar Nucleophiles to Alkynes 3.3 Stereospecific Cyclopropanation 3.4 Gold-Carbon Bonding in Cationic Intermediates and Relativistic Effects 3.5 A Bonding Model for Gold(I)-Carbene Complexes 4 Further Insights into Reactivity from Gold-Catalyzed Cycloisomerization Reactions 4.1 Intramolecular Rearrangements of 1,5-Enynes 4.2 Ligand- and Substrate-Controlled Access to [2+2], [3+2], [4+2], and [4+3] Cycloadditions in Gold-Catalyzed Reactions of Allene-Enes 5 Intermolecular Annulation Reactions 5.1 A [4+3] Annulation Approach to Azepines 5.2 Orbital Considerations in [3+3] Annulations 6 Tandem Reactions 7 Conclusions

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关键词：

gold catalysis enantioselective catalysis cycloisomerizations alkynes allenes

DOI：

10.1055/s-0029-1219369

被引量：

453

年份：

2010