Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 86, Issue 17, Pages 12367-12377Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.1c01315
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Funding
- National Research Foundation of Korea [NRF-2018R1A6A1A03023718, NRF-2020R1A2C2005961]
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The novel domino mode of assembly discovered in a one-pot three-component reaction under mild and eco-friendly conditions led to the synthesis of a new tricyclic skeleton, involving consecutive formation of multiple bonds and construction of two rings in a diastereoselective manner.
A new domino mode of assembly was discovered from the one-pot three-component reactions of pyrrole derivatives, active methylene compounds (malononitrile, methyl cyanoacetate, or ethyl cyanoacetate), and sodium cyanide in the presence of piperidinium acetate in EtOH at room temperature, leading to a novel tricyclic skeleton in excellent yield under mild and eco-friendly conditions. This well-choreographed domino process enabled formation of multiple bonds (three C-C and one C-O) for consecutive construction of two rings (pyrrolidine and dihydrofuran) in a diastereoselective manner.
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