Shape and Stereoselective Cyclopropanation of Alkenes Catalyzed by Iron Porphyrins Robbins Wolf, Jennifer Hamaker, Christopher Woo, L. Djukic, Jean-Pierre Kodadek, Thomas Woo, L. Keith
dc.contributor.department Chemistry 2018-02-17T09:18:22.000 2020-06-30T01:22:23Z 2020-06-30T01:22:23Z Sun Jan 01 00:00:00 UTC 1995 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="" target="_blank">10.1021/ja00141a011</a>. Copyright 1995 American Chemical Society.</p>
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dc.identifier.articleid 1738
dc.identifier.contextkey 7962004
dc.identifier.s3bucket isulib-bepress-aws-west
dc.identifier.submissionpath chem_pubs/722
dc.language.iso en
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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
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relation.isOrgUnitOfPublication 42864f6e-7a3d-4be3-8b5a-0ae3c3830a11
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