Modular One-Step Three-Component Synthesis of Tetrahydroisoquinolines Using a Catellani Strategy
| Autor: | Shijun Gao, Siwei Zhou, Qianghui Zhou, Miao Bai, Wei Yan, Hong-Gang Cheng, Han Chen, Guangyin Qian |
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| Rok vydání: | 2018 |
| Předmět: |
010405 organic chemistry
Chemistry business.industry chemistry.chemical_element Regioselectivity One-Step General Medicine General Chemistry Modular design 010402 general chemistry 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences chemistry.chemical_compound Atom economy Yield (chemistry) business Norbornene Palladium |
| Zdroj: | Angewandte Chemie International Edition. 57:10980-10984 |
| ISSN: | 1433-7851 |
| DOI: | 10.1002/anie.201806780 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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