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3.6.14.1 Asymmetric Gold-Catalyzed Transformations

DOI: 10.1055/sos-SD-103-00072

Campbell, M. J.; Toste, F. D.Science of Synthesis Knowledge Updates, (20123123.

General Introduction

Homogeneous gold catalysis has seen tremendous developmental growth over the past 10 years. The seminal reports documenting its potential utility were just appearing at the same time as catalysis using other main-block transition metals was maturing, research for which the Nobel Prize was awarded in 2001, 2005, and 2010. Gold salts were initially thought to be largely devoid of catalytic activity and were initially overlooked because they do not readily cycle through oxidation states within a system; indeed, this prohibits most catalysis that requires oxidative addition and reductive elimination processes. However, it also provides orthogonal reactivity relative to other metals and permits an array of unique transformations. Secondly, an initial lack of asymmetric gold-catalyzed reactions raised debate as to whether ligands could be identified that overcome the natural limitations of the linear geometry of gold(I). Further research has now affirmed that common ligand scaffolds are often suitable, but the challenges have resulted in some unusual solutions. For example, the first highly enantioselective catalysis using chiral counterions has been reported using gold(I).

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References