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Modular One-Step Three-Component Synthesis of Tetrahydroisoquinolines Using a Catellani Strategy
Guangyin Qian1, Miao Bai1, Shijun Gao1
1College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, China.
Abstract:
Reported is a modular one-step three-component synthesis of tetrahydroisoquinolines using a Catellani strategy. This process exploits aziridines as the alkylating reagents, through palladium/norbornene cooperative catalysis, to enable a Catellani/Heck/aza-Michael addition cascade. This mild, chemoselective, and scalable protocol has broad substrate scope (43 examples, up to 90 % yield). The most striking feature of this protocol is the excellent regioselectivity and diastereoselectivity observed for 2-alkyl- and 2-aryl-substituted aziridines to access 1,3-cis-substituted and 1,4-cis-substituted tetrahydroisoquinolines, respectively. Moreover, this is a versatile process with high step and atom economy.
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