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      Designing ‘Totem’C2-Symmetrical Iron Porphyrin Catalysts for Stereoselective Cyclopropanations

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          Diels-alder in aqueous molecular hosts: unusual regioselectivity and efficient catalysis.

          Self-assembled, hollow molecular structures are appealing as synthetic hosts for mediating chemical reactions. However, product binding has inhibited catalytic turnover in such systems, and selectivity has rarely approached the levels observed in more structurally elaborate natural enzymes. We found that an aqueous organopalladium cage induces highly unusual regioselectivity in the Diels-Alder coupling of anthracene and phthalimide guests, promoting reaction at a terminal rather than central anthracene ring. Moreover, a similar bowl-shaped host attains efficient catalytic turnover in coupling the same substrates (although with the conventional regiochemistry), most likely because the product geometry inhibits the aromatic stacking interactions that attract the planar reagents to the host.
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            Stereoselective cyclopropanation reactions.

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              Heterocycles from cyclopropanes: applications in natural product synthesis.

              The construction of heterocyclic compounds from activated cyclopropane derivatives offers an alternative strategy for the preparation of molecules that may be of interest from a structural or biological standpoint. Several newly developed methods provide access to densely functionalized heterocycles in a manner that can be considered useful for both diversity- and target-oriented synthetic approaches. This tutorial review focuses on the latter, describing recent developments and applications of cyclopropane ring-expansion reactions in natural product synthesis.
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                Author and article information

                Journal
                Chemistry - A European Journal
                Chem. Eur. J.
                Wiley
                09476539
                September 12 2016
                September 12 2016
                August 24 2016
                : 22
                : 38
                : 13599-13612
                Affiliations
                [1 ]Department of Chemistry; University of Milan; Via C. Golgi 19 20133 Milan Italy
                [2 ]Institut des Sciences Chimiques de Rennes; Université de Rennes 1; 263 avenue du Général Leclerc 35042 Rennes Cedex France
                [3 ]Department of Chemistry; University of Pavia; Via Taramelli 12 27100 Pavia Italy
                Article
                10.1002/chem.201602289
                © 2016

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