Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 83, Issue 16, Pages 9471-9477Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.8b00917
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Funding
- SERB-DST India [EMR/2014/000395]
- CSIR India
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A novel (3 + 3) annulation approach has been developed for the synthesis of 2-aryl terephthalates from nitroallylic acetates and stabilized sulfur ylides. The 2-aryl terephthalates, which are also biaryls bearing a terephthalate moiety, are formed through a cascade of reactions such as a gamma-selective S(N)2' reaction, gamma-selective intramolecular Michael addition, and two eliminations in the presence of Cs2CO3 in CH3CN at room temperature. The products are formal precursors of farnesyltransferase inhibitors and are also potential monomers in polymer chemistry.
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