Gold(I)-Catalyzed Enantioselective Intramolecular Hydroamination of Allenes

Asymmetric Gold‐Catalyzed Hydroarylation/Cyclization Reactions

“…The influence of silver salts was investigated ( Table 1, entries 2-4), silver triflate and silver bis(trifluoromethanesulfonyl)imidate giving the best results. The use of silver benzoate [9] was particularly striking as no conversion was observed at room temperature for 240 h ( Table 1, entry 2). Lowering the temperature to 0 8C increased the re-action time but moderately influenced the enantiomeric excesses (Table 1, entries 5-8).…”

An Efficient Domino Approach for the Synthesis of Multisubstituted Pyrroles via Gold/Silver‐Catalyzed Amination/Cycloisomerization of (Z)‐2‐En‐4‐yn‐1‐ols

“…Based on this work, we envisioned that pyrroles might be constructed directly from (Z)-enynols. Herein, we describe our study of this new approach which combines an initial Au/Ag-catalyzed amination of (Z)-enynols followed by an intramolecular hydroA C H T U N G T R E N N U N G amination [12] (or cycloisomerization) of the alkyne moiety in a one-pot procedure, [13] and there is no need to isolate the intermediate enynamines (Scheme 1).…”

Fluorocarbon compatibilized gold-silica nanocomposites for recyclable regioselective hydroamination of alkynes in a fluorous biphasic system

“…Late transition metals (Ir, Pd, Au, Rh) are highly attractive and desirable for asymmetric hyroaminations due to higher functional group tolerance for both inert-and intramolecular variants, lowest air and moisture sensitivity and provide higher enantioselectivities [19]. However, to date there are only a few reports of gold-catalyzed enantioselective hydroamination reactions, for instance the catalysts reported were dinuclear gold(I)-phosphine complexes with biaryl-based backbone [20]. We sought to use an alternative method whereby in line with previous work on silica supported metal nanoparticles in our lab [21], to design and synthesize perfluorocarbon compatibilized gold-silica supported nanoparticles.…”