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

Date
2006
Authors
Dhoro, Francis
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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.
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Thesis (M.S.)--University of Hawaii at Manoa, 2006.
Includes bibliographical references (p. 63).
xi, 101 leaves, bound ill. 29 cm
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Ring formation (Chemistry), Alkylation
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Theses for the degree of Master of Science (University of Hawaii at Manoa). Chemistry; no. 4056
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