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Part I, Interrupted Nazarov cyclization on silica gel: Part II, Tandem alkylation-cyclization process via an O,C dianion
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|Title:||Part I, Interrupted Nazarov cyclization on silica gel: Part II, Tandem alkylation-cyclization process via an O,C dianion|
|Keywords:||Ring formation (Chemistry)|
|Abstract:||Part 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.|
|Description:||Thesis (M.S.)--University of Hawaii at Manoa, 2006.|
Includes bibliographical references (p. 63).
xi, 101 leaves, bound ill. 29 cm
|Rights:||All 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.|
|Appears in Collections:||M.S. - Chemistry|
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