Cyclopropanes are systems being high in energy. Therefore, these entities are ideally suited for a cascade of consecutive reactions, so called domino reactions. Such transformations based on ring-enlargement reactions of donor-acceptor-substituted cyclopropanes are discussed.1 Aldehyde, ketimines and thioketones are utilized as acceptors whereas ether moieties serve as donor.2 A rearrangement leads to the respective five-membered rings which tend to eliminate water. As a result, aromatic systems are formed.2 Depending on the substrate domino cascades are initiated which are able to transform the biscyclopropane derivative 1  in one step into the corresponding quaterpyrrol 2  .2 References [1] T. F. Schneider, J. Kaschel, D. B. Werz, Angew. Chem. Int. Ed. 2014  , 53, in press.[2] a) T. F. Schneider, J. Kaschel, B. Dittrich, D. B. Werz, Org. Lett. 2009  , 11, 2317-2320; b) T. F. Schneider, J. Kaschel, S. I. Awan, B. Dittrich, D. B. Werz, Chem. Eur. J. 2010  , 16, 11276-11288; c) J. Kaschel, T. F. Schneider, D. Kratzert, D. Stalke, D. B. Werz, Angew. Chem. Int. Ed. 2012  , 51, 11153-11156; d) J. Kaschel, C. D. Schmidt, M. Mumby, D. Kratzert, D. Stalke, D. B. Werz, Chem. Commun. 2013  , 49, 4403-4405.

Oligopyrrole synthesis by domino reactions of donor-acceptor cyclopropanes

248th National Meeting (2014)

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