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Stereoselective Double Lewis Acid/Organo-Catalyzed Dimerization of Donor-Acceptor Cyclopropanes into Substituted 2-Oxabicyclo[3.3.0]octanes

  作者 NOVIKOV ROMAN A; TIMOFEEV VLADIMIR P; TOMILOV YURY V  
  选自 期刊  Journal of Organic Chemistry;  卷期  2012年77-14;  页码  5993-6006  
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[摘要]A new approach for the dimerization of donor acceptor cyclopropanes (2-arylcyclopropane-1,1-dicarboxylates) under double-catalysis conditions by treatment with 20 mol % of GaCl3 and dimethyl 3,5-dimethyl-1-pyrazoline-3,5-dicarboxylate as a specific organocatalyst has been found. Under these conditions, the starting compounds are regio- and stereospecifically converted into polysubstituted 2-oxabicyclo[3.3.0]octanes. Two new rings, one C-O bond, and two C-C bonds are formed in this process, and four stereocenters are thus created. The reaction mechanism was thoroughly studied by NMR spectroscopy, and a number of intermediates were detected.

 
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