Journal
ORGANIC LETTERS
Volume 22, Issue 23, Pages 9337-9341Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c03552
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Funding
- Ministry of Science and Technology, Taiwan [MOST 108-2113-M-039-006]
- China Medical University [CMU 108-MF-72]
- Chung Shan Medical University [CSMU-INT-108-11]
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Palladium-catalyzed intramolecular tandem cyclization reactions were conducted for the synthesis of densely cis/cisfused aza-tetracydic structures. The process involved a palladium(II)-catalyzed aerobic aza-Wacker reaction, followed by a palladium(0)-catalyzed Heck reaction. The effects of the solvent and benzene substitution pattern on the one-pot, two-step cascade reaction were studied systematically, and a probable mechanism was proposed. Strained pentahydrobenzo[f]cyclopenta[hdindolizin-6-one and racemic gamma-lycorane can also be synthesized rapidly using this palladium-catalyzed aza-Wacker-Heck cyclization reaction.
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