Please use this identifier to cite or link to this item: http://hdl.handle.net/10125/20467

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

File Description SizeFormat 
M.S.Q111.H3_4056_uh.pdfVersion for UH users1.42 MBAdobe PDFView/Open
M.S.Q111.H3_4056_r.pdfVersion for non-UH users. Copying/Printing is not permitted1.42 MBAdobe PDFView/Open

Item Summary

Title: Part I, Interrupted Nazarov cyclization on silica gel: Part II, Tandem alkylation-cyclization process via an O,C dianion
Authors: Dhoro, Francis
Keywords: Ring formation (Chemistry)
Alkylation
Issue Date: 2006
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
URI/DOI: http://hdl.handle.net/10125/20467
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



Items in ScholarSpace are protected by copyright, with all rights reserved, unless otherwise indicated.