Shape and Stereoselective Cyclopropanation of Alkenes Catalyzed by Iron Porphyrins

dc.contributor.author Robbins Wolf, Jennifer
dc.contributor.author Hamaker, Christopher
dc.contributor.author Woo, L.
dc.contributor.author Djukic, Jean-Pierre
dc.contributor.author Kodadek, Thomas
dc.contributor.author Woo, L. Keith
dc.contributor.department Chemistry
dc.date 2018-02-17T09:18:22.000
dc.date.accessioned 2020-06-30T01:22:23Z
dc.date.available 2020-06-30T01:22:23Z
dc.date.copyright Sun Jan 01 00:00:00 UTC 1995
dc.date.issued 1995-09-01
dc.description.abstract <p>Iron porphryin complexes are active catalysts for the cyclopropanation of alkenes by ethyl diazoacetate. Fe(TIP) (TIP = meso-tetra-p-tolylporphyrin), an isolated iron(II) porphyrin complex, can be used as the catalyst, or the iron(III) complexes of several porphyrins can be reduced in situ. The reactions produce synthetically useful excesses of the trans cyclopropyl ester products. This stereoselectivity exhibits a modest solvent dependence, with donor solvents giving higher ratios of the trans cyclopropane products. The diastereoselectivity exhibits only a modest dependence on the steric bulk of the porphyrin. The reactions are selective for 1-alkenes and 1, 1-disubstituted alkenes. Conjugated substrates and enol ethers react more rapidly than simple aliphatic alkenes. A mechanistic model for the iron-mediated reactions is proposed which is consistent with the data presented herein.</p>
dc.description.comments <p>Reprinted (adapted) with permission from <em>Journal of the American Chemical Society </em>117 (1995): 9194, doi:<a href="http://dx.doi.org/10.1021/ja00141a011" target="_blank">10.1021/ja00141a011</a>. Copyright 1995 American Chemical Society.</p>
dc.format.mimetype application/pdf
dc.identifier archive/lib.dr.iastate.edu/chem_pubs/722/
dc.identifier.articleid 1738
dc.identifier.contextkey 7962004
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath chem_pubs/722
dc.identifier.uri https://dr.lib.iastate.edu/handle/20.500.12876/15209
dc.language.iso en
dc.source.bitstream archive/lib.dr.iastate.edu/chem_pubs/722/0-L_1995_Woo_ShapeStereoselective.pdf|||Sat Jan 15 01:44:42 UTC 2022
dc.source.bitstream archive/lib.dr.iastate.edu/chem_pubs/722/1995_Woo_ShapeStereoselective.pdf|||Sat Jan 15 01:44:44 UTC 2022
dc.source.uri 10.1021/ja00141a011
dc.subject.disciplines Chemistry
dc.title Shape and Stereoselective Cyclopropanation of Alkenes Catalyzed by Iron Porphyrins
dc.type article
dc.type.genre article
dspace.entity.type Publication
relation.isAuthorOfPublication d17ef200-84b4-46b1-94f3-67cc67f0a33f
relation.isOrgUnitOfPublication 42864f6e-7a3d-4be3-8b5a-0ae3c3830a11
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