Pd-Catalyzed Carboamination Reactions for the Synthesis of Imidazolidin-2-ones and Related Heterocycles.
dc.contributor.author | Fritz, Jonathan A. | en_US |
dc.date.accessioned | 2009-09-03T14:44:43Z | |
dc.date.available | NO_RESTRICTION | en_US |
dc.date.available | 2009-09-03T14:44:43Z | |
dc.date.issued | 2009 | en_US |
dc.date.submitted | en_US | |
dc.identifier.uri | https://hdl.handle.net/2027.42/63693 | |
dc.description.abstract | Imidazolidin-2-ones and related heterocycles have many medicinal and synthetic uses. Progress toward expanding the scope of Pd-catalyzed carboamination to include the synthesis of these classes of heterocycles is demonstrated. 4,4- and 4,5-disubstituted imidazolidin-2-ones were generated in high yield from N-allylureas and aryl bromides. 4,5-disubstituted imidazolidin-2-ones and imidazolidin-2-ones derived from internal olefins were made in moderate to high diastereoselectivity. Vinyl halides were also shown to be effective coupling partners. Orthoganol deprotection of an N1-benzyl N3 p-methoxyphenyl protected imidazolidin-2-ones was achieved. An enantioselective synthesis of imidazolidin-2-ones using chiral ligands or chiral auxiliaries was pursued. Lastly, studies on the Pd-catalyzed carboamination of N-allylguanidines, O-allylcarbamate, homoallylsulfoximines, and N-allylsulfamides are described. | en_US |
dc.format.extent | 923218 bytes | |
dc.format.extent | 1373 bytes | |
dc.format.mimetype | application/pdf | |
dc.format.mimetype | text/plain | |
dc.language.iso | en_US | en_US |
dc.subject | Pd-Catalysis | en_US |
dc.subject | Imidazolidin-2-Ones | en_US |
dc.subject | Carboamination | en_US |
dc.subject | Cyclic Ureas | en_US |
dc.subject | Cyclic Sulfamides | en_US |
dc.subject | Aminopalladation | en_US |
dc.title | Pd-Catalyzed Carboamination Reactions for the Synthesis of Imidazolidin-2-ones and Related Heterocycles. | en_US |
dc.type | Thesis | en_US |
dc.description.thesisdegreename | PhD | en_US |
dc.description.thesisdegreediscipline | Chemistry | en_US |
dc.description.thesisdegreegrantor | University of Michigan, Horace H. Rackham School of Graduate Studies | en_US |
dc.contributor.committeemember | Wolfe, John P. | en_US |
dc.contributor.committeemember | Montgomery, John | en_US |
dc.contributor.committeemember | Sanford, Melaine S. | en_US |
dc.contributor.committeemember | Sherman, David H. | en_US |
dc.subject.hlbsecondlevel | Chemistry | en_US |
dc.subject.hlbtoplevel | Science | en_US |
dc.description.bitstreamurl | http://deepblue.lib.umich.edu/bitstream/2027.42/63693/1/jafri_1.pdf | |
dc.owningcollname | Dissertations and Theses (Ph.D. and Master's) |
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