3 years ago

Palladium-Catalyzed α-Arylation of Silylenol Ethers in the Synthesis of Isoquinolines and Phenanthridines

Palladium-Catalyzed α-Arylation of Silylenol Ethers in the Synthesis of Isoquinolines and Phenanthridines
Pravin Kumar, Gangam Srikanth Kumar, Gaurav Saini, Manmohan Kapur, Arun Raj Kizhakkayil Mangadan
A diverse array of isoquinolines and phenanthridines have been accessed by developing a two-step, one-pot method constituting regioselective palladium-catalyzed Kuwajima–Urabe α-arylation of silylenol ethers and acid-mediated deprotection, annulation, and aromatization. Structural diversity in the silylenol ethers leads to three different classes of isoquinolines and phenanthridines from which related natural products can be derived. The synthetic utility of this method by the quick assembly of the natural product trispheridine is also demonstrated.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b03776

DOI: 10.1021/acs.orglett.7b03776

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