Recent Developments in Asymmetric Catalysis in the Presence of Chiral Gold Complexes

• Published in: Synthesis (Stuttgart) 2011-05, Vol.2011 (10), p.1501-1514
• Main Authors: Pradal, Alexandre, Toullec, Patrick Y., Michelet, Véronique
• Format: Article
• Language: English
• Subjects: Catalysis; Catalysts: preparations and properties; Chemistry; Exact sciences and technology; General and physical chemistry; Kinetics and mechanisms; Organic chemistry; Reactivity and mechanisms; review; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
• ISSN: 0039-7881; 1437-210X
• DOI: 10.1055/s-0030-1258465

Abstract Catalytic asymmetric gold-catalyzed reactions provide versatile routes to enantiomerically enriched carbo- and heterocycles. This review summarizes the recent work on the development of novel catalytic systems combining gold and a chiral ligand. 1 Introduction 2 Gold-Catalyzed Activation of Carbonyl and Imine-Type Bonds 3 Gold-Catalyzed Activation of Alkenes 3.1 Hydrogenation Reactions 3.2 Nucleophilic Additions to Alkenes 4 Gold-Catalyzed Activation of Allenes 4.1 In the Presence of a Chiral Gold Complex 4.1.1 Oxygen Nucleophiles 4.1.2 Nitrogen Nucleophiles 4.1.3 Carbon Nucleophiles 4.2 In the Presence of a Chiral Silver Salt 5 Gold-Catalyzed Activation of Alkynes 5.1 Rearrangement of Propargylic Esters 5.2 Desymmetrization Reactions 5.3 Cycloisomerization of Enynes 5.3.1 In the Absence of an External Nucleophile 5.3.2 In the Presence of a Nucleophile: Domino Processes 5.3.2.1 Oxygen and Nitrogen Nucleophiles 5.3.2.2 Carbon Nucleophiles 6 Conclusion