Journal
BULLETIN OF THE KOREAN CHEMICAL SOCIETY
Volume 39, Issue 5, Pages 651-656Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/bkcs.11445
Keywords
Gold catalyst; [2+2] cyclization; Propargylic carboxylate; Bicyclo[3,2,0]heptane
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Funding
- National Research Foundation of Korea (NRF) - Korean Government, through the Center for New Directions in Organic Synthesis [NRF-2014R1A5A1011165]
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Propargylic pivaloates bearing an alkynyl group at a three-carbon tether under the gold catalysis would undergo [3,3] rearrangements of propargylic pivaloates followed by tandem [2+2] cyclization to give the corresponding 6-acylbicyclo[3,2,0]hept-6-ens. In continuing work, we prepared various substrates bearing two arms of alkyne-propargylic pivaloates to explore primitive dendrimer concept bicyclic compounds. Finally, we could obtain a series of diasteromeric compounds bearing two arms of 6-acylbicyclo[3,2,0]hept-6-ene groups in high yields.
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