期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 78, 期 8, 页码 3832-3846出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo400246d
关键词
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资金
- NIH via the KU Center for Methodology and Library Development [P 50 GM063966]
- NSF-MRI [CHE-0923449]
Cu-catalyzed three-component coupling of imines with benzoyl chloride and terminal arylalkynes followed by enyne ring-closing metathesis (RCM) and Heck cyclization afforded medicinally relevant benzoindolines, cyclopropane-fused indenopyridines, pyrroloquinolines, or 1,7-tetrahydrophenanthrolines via divergent cyclization pathways. Unexpectedly, the Pd-catalyzed cyclization of heterocyclic dienes proceeded via regiodivergent 5-exo or 6-endo pathways depending on the ring size (n = 1, 2) or the presence of isosteric groups (CH vs N). A one pot protocol for the enyne-RCM/Heck annulation featuring a sequential addition of the Ru and Pd catalysts was developed maximizing the synthetic efficiency.
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