Domino Reactions with Three-Membered Rings and Triple Bonds
Daniel B. Werz
Institute for Organic Chemistry, Technical University of Braunschweig, Germany
Cyclopropanes as well as carbon-carbon triple bonds are systems being high in energy.
Therefore, both moieties are ideally suited for a cascade of consecutive reactions (domino
reactions).
In a first part, domino reactions based on ring-enlargement reactions of donor-acceptorsubstituted cyclopropanes[1] are discussed. 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.
In a second part, Pd-catalyzed domino reactions starting with triple bonds attached to
carbohydrate derivatives 4 are reported to construct a variety of chroman- and isochromantype structures such as 5.[3] Such domino sequences are also employed to a variety of other
processes leading to complex scaffolds in a facile and efficient fashion.
[1] H.-U. Reißig, R. Zimmer, Chem. Rev. 2003, 103, 1151-1196.
[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.
[3] a) M. Leibeling, D. C. Koester, M. Pawliczek, S. C. Schild, D. B. Werz, Nature Chem. Biol. 2010, 6, 199-201; b)
M. Leibeling, B. Milde, D. Kratzert, D. Stalke, D. B. Werz, Chem. Eur. J. 2011, 17, 9888-9892; c) M. Leibeling, D.
B. Werz, Chem. Eur. J. 2012, 18, 6138-6141; d) M. Leibeling, M. Pawliczek, D. Kratzert, D. Stalke, D. B. Werz,
Org. Lett. 2012, 14, 346-349.