Show simple item record
dc.creatorPark, Gyoosoon
dc.description.abstractMy research objective was to investigate two-step intramolecular nucleometallationcoupling reactions of allenes to form polyfiinctional heterocyclic molecules. This reaction sequence takes place by either: a) an intramolecular oxy- or aminomercuration of an allene followed by a transmetallation of the mercury by palladium(II), then a coupling reaction (e.g., with carbon monoxide and an alcohol to form estCTs); or b) an intramolecular oxy- or aminopalladation of an allene followed, in situ, by the coupling. The results of this investigation have led to: 1) the development of a stereospecific approach to cis-2-15-alkyltetrahydrofiiran-2-yl)-2-propenoates; 2) the discovery of a stereospecific reduction of cis-2-(5-alkyltetrahydrofuran-2-yl)-2-propenoates; and 3) the development of a general synthetic approach to natural and unnatural nonactic acid esters. Scheme 1 represents our basic idea for the intramolecular nucleometallation of allenes (1) using mercury or palladium salts. A metal-complexed allene (2) should cyclize to form an intermediate a-vinyl complex of the metal (3). The complex 3 (where M = palladium) can undergo carbonylation and alkoxide coupling in the presence of carbon monoxide and an alcohol to form substituted acrylate esters (4) which should be valuable intermediates for organic synthesis.
dc.publisherTexas Tech Universityen_US
dc.subjectOrganic compounds -- Synthesisen_US
dc.subjectPalladium catalystsen_US
dc.subjectTetrahydrofuran -- Synthesisen_US
dc.subjectAllene -- Synthesisen_US
dc.titleStereoselective syntheses of functionalized tetrahydrofurans via intramolecular oxymetallations of allenes and syntheses of methyl nonactate homologues

Files in this item


There are no files associated with this item.

This item appears in the following Collection(s)

Show simple item record