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DOI: 10.1055/s-0029-1219369
A Reactivity-Driven Approach to the Discovery and Development of Gold-Catalyzed Organic Reactions
Publikationsverlauf
Publikationsdatum:
08. Februar 2010 (online)
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Abstract
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
Key words
gold catalysis - enantioselective catalysis - cycloisomerizations - alkynes - allenes
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