Broad Scope Aminocyclization of Enynes with Cationic JohnPhos–Gold(I) Complex as the Catalyst

Abstract

A practical aminocyclization of 1,6-enynes with a wide variety of substituted anilines, including N-alkyl anilines, has been achived by using cationic [JohnPhosAu(MeCN)]SbF6 as a general purpose catalyst. The resulting adducts can be easily converted into polycyclic compounds by palladium- and gold-catalyzed reactions.

Inter/Intramolecular Cascade of 1,6-Enynes Catalyzed by All-Metal Aromatic Tripalladium Complexes and Carboxylic Acids

“…Product 1v was prepared following a reported procedure and was isolated (silica gel, n -hexane/EtOAc 8:2) as a white solid (212 mg, 0.9 mmol, 71%). The spectral data for this compound correspond to the literature …”

“…The spectral data for this compound correspond to the literature. 50 4′-Methylene-1′,2-ditosyl-1,2,3,4,6,7-hexahydrospiro-[isoindole-5,3′-pyrrolidine] (2a). Compound 2a (33.6 mg, 0.067 mmol, 45% yield) was obtained as a colorless oil (silica gel, nhexanes/EtOAc, gradient) following the general procedure GP-1 from 1a (0.3 mmol); 1 H NMR (300 MHz, CDCl 3 ) δ 7.69 (dd, J = 17.6, 8.3 Hz, 4H), 7.33 (dd, J = 7.7, 5.3 Hz, 4H), 4.87 (t, J = Hz, 1H), 4.73 (t, J = 2.4 Hz, 1H), 3.97 (m, 2H), 3.85 (m, 4H), 2.99−2.92 (m, 2H), 2.44 (s, 6H), 1.91−1.84 (m, 4H), 1.67−1.47 (m, 2H).…”

A dual-metal catalyzed sequential cascade reaction in an engineered protein cage

“…[31] Notably, we herein report the first examples of RuH-type catalyzed alloc-deprotection of secondary amines in aqueous buffer. In order to identify a suitable gold-complex for catalyzing the second reaction step, three different gold complexes (Au1, Au2, Au3, see Figure 1C) were synthesized according to reported procedures [26,32,33] and their reactivity was compared by studying the ring-closing reaction of intermediate I1 to indole product P1 in aqueous as well as protein containing solutions (see Figure 1B). Of the catalysts compared, only Au3 catalyzed hydroamination reactions in the presence of BSA and was therefore studied further.…”

Gold(I)‐Catalysis for the Synthesis of Terpenoids: From Intramolecular Cascades to Intermolecular Cycloadditions

“…The addition of heteronucleophiles such as water, alcohols, or amines to 1,6‐enynes leads to products of hydroxy‐, alkoxy‐ or aminocyclization of type 8 by the stereospecific opening of intermediates 2 under milder conditions than those required by other metal catalysts (Scheme ) ,,,,,,,,. Addition of heteronucleophiles to 1,5‐, and 1,7‐enynes occurs through similar mechanisms.…”