Cinchona alkaloids annulation

One-pot annulation of 2-naphthol analogs to heterocycles 12COS613. Organocatalytic asymmetric halocyclization (among catalysts are bis-cinchona alkaloids and chiral trisimidazolines) 13H(87)763. Photoredox functionalization of C—H bonds adjacent to a nitrogen atom 12CSR7687. 

In this work, the combination of cinchona-alkaloid-derived primary amine and Au(I) phosphine complex has been employed to effect two consecutive Friedel-Crafts-type reactions of pyrrole in one pot to furnish 2,3-annulated pyrroles containing a seven-membered ring (eq 1) This reaction proceeds through initial asymmetric 1,4-addition of p)rrole to enones catalyzed by the primary amine followed by an intramolecular 7-c/ido-dig cycliza-tion catalyzed by the Au(I) phosphine complex. 

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