Abstract
The reactions of diazo esters with 2-arylcyclopropane-1,1-dicarboxylates, the represen- tatives of donor-acceptor cyclopropanes (DACs), mediated by Sc(OTf)3, SnCl4, and GaCl3 proceeded with nitrogen elimination to give the C—C coupling products. No products of the formal [3+3] cycloaddition of diazo compounds to DACs were formed but the main reaction direction was addition of diazo ester to either 1,3- or 1,2-zwitterions generated upon Lewis acid-mediated cyclopropane ring opening giving rise to new 1,4- and 1,3-zwitterionic inter- mediates. The formed intermediates underwent further fragmentations and rearrangements to give substituted cyclopropanedi-, -tri-, and -tetracarboxylates. Mechanistic aspects of the observed reactions were discussed.
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Novikov, R.A., Borisov, D.D. & Tomilov, Y.V. Lewis acid-mediated reactions of donor-acceptor cyclopropanes with diazo esters. Russ Chem Bull 67, 265–273 (2018). https://doi.org/10.1007/s11172-018-2069-8
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DOI: https://doi.org/10.1007/s11172-018-2069-8