Part I, Interrupted Nazarov cyclization on silica gel: Part II, Tandem alkylation-cyclization process via an O,C dianion

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dc.contributor.authorDhoro, Francis
dc.date.accessioned2011-07-21T23:04:37Z
dc.date.available2011-07-21T23:04:37Z
dc.date.issued2006
dc.descriptionThesis (M.S.)--University of Hawaii at Manoa, 2006.
dc.descriptionIncludes bibliographical references (p. 63).
dc.descriptionxi, 101 leaves, bound ill. 29 cm
dc.description.abstractPart I: Exposure of a mixture of propargyl vinyl ketone and a nucleophilic primary or secondary amine to activated dry silica gel in the absence of solvent leads to a cascade of reactions that results in the formation of an aminocyclopentenone. The reaction with triethylamine leads to a cross-conjugated cyclopentadienone. Part II: A general protocol for preparing densely functionalized cyclopentenones through a tandem alkylation-cyclization process is described. Addition of lithioallene 1.11 to enamide 1.5 generates tetrahedral intermediate 1.12. Deprotonation of the γ-carbon atom of the allene function in situ. followed by trapping by a suitable electrophile and cyclization during workup leads to C6 substituted cyclopentenone 1.14.
dc.identifier.urihttp://hdl.handle.net/10125/20467
dc.language.isoen-US
dc.relationTheses for the degree of Master of Science (University of Hawaii at Manoa). Chemistry; no. 4056
dc.rightsAll UHM dissertations and theses are protected by copyright. They may be viewed from this source for any purpose, but reproduction or distribution in any format is prohibited without written permission from the copyright owner.
dc.subjectRing formation (Chemistry)
dc.subjectAlkylation
dc.titlePart I, Interrupted Nazarov cyclization on silica gel: Part II, Tandem alkylation-cyclization process via an O,C dianion
dc.typeThesis
dc.type.dcmiText

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