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Alkylgold(I) complexes were formed from the gold(I)-promoted intramolecular addition of various amine nucleophiles to alkenes. These experiments provide the first direct experimental evidence for the elementary step of gold-promoted nucleophilic addition to an alkene. Deuterium-labeling studies and X-ray crystal structures provide support for a mechanism involving anti-addition of the nucleophile to a gold-activated alkene, which is verified by DFT analysis of the mechanism. Ligand studies indicate that the rate of aminoauration can be drastically increased by use of electron-poor arylphosphines, which are also shown to be favored in ligand exchange experiments. Attempts at protodeauration lead only to recovery of the starting olefins, though the gold can be removed under reducing conditions to provide the purported hydroamination products.

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In control: Gold(I)‐catalyzed intramolecular addition of silyl enol ethers to alkynes and allenes allows for the diastereoselective synthesis of cyclopentenes with control of the position of the double bond. The utility of these reactions is demonstrated by an efficient total synthesis of (+)‐lycopladine A that takes advantage of the orthogonal reactivity of AuI and Pd0 towards unsaturated iodides (see scheme).

Chiral ligands (L*) and chiral anions [(S)-TriPAg] are employed in the gold(I)-catalyzed enantioselective intramolecular additions of hydrazines and hydroxylamines to allenes. These complementary methods allow access to chiral vinyl isoxazolidines, oxazines, and differentially protected pyrazolidines. PNB=para-nitrobenzoy

A strategy for incorporating social justice themes into an introductory organic chemistry curriculum is described. We have deliberately infused social justice themes into the standard organic chemistry curriculum by discussing the history and social impact of key compounds. Using these key compounds that have had significant social, cultural, and environmental impacts, students practiced arrow-pushing mechanisms, predicted products, and identified pK a values and functional groups. We believe this approach helps make the material more relevant to students, keep students engaged, and emphasize the real-world applications of the concepts and compounds that they are learning about. Details on the implementation and the evaluation of this work are discussed.

Unter Kontrolle: Durch Gold(I)‐katalysierte intramolekulare Addition von Silylenolethern an Alkine und Allene gelingt die diastereoselektive Synthese von Cyclopentenen mit festgelegter Position der Doppelbindung. Dies wird anhand einer effizienten Totalsynthese von (+)‐Lycopladin A gezeigt, die die orthogonale Reaktivität von AuI und Pd0 gegenüber ungesättigten Iodiden vorteilhaft nutzt (siehe Schema).

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