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dc.contributor.authorBuckley, B.
dc.contributor.authorBoxhall, J.
dc.contributor.authorPage, P.
dc.contributor.authorChan, Y.
dc.contributor.authorElsegood, M.
dc.contributor.authorHeaney, H.
dc.contributor.authorHolmes, K.
dc.contributor.authorMcildowie, M.
dc.contributor.authorMcKee, V.
dc.contributor.authorMcGarth, M.
dc.contributor.authorMocerino, Mauro
dc.contributor.authorPoulton, A.
dc.contributor.authorSampler, E.
dc.contributor.authorSkelton, B.
dc.contributor.authorWhite, A.
dc.identifier.citationBuckley, Benjamin and Boxhall, Jonathan and Page, Philip and Chan, Yohan and Elsegood, Mark and Heaney, Harry and Holmes, Kathryn and Mcildowie, Matthew and McKee, Vickie and McGrath, Matthew and Mocerino, Mauro and Poulton, Andrew and Sampler, Edward and Skelton, Brian and White, Allan. 2006. Mannich and O-Alkylation Reactions of Tetraalkoxyresorcin[4]arenes. The Use of Some Products in Ligand-Assisted Reactions. European Journal of Organic Chemistry 2006 (22): 5117-5134.

The measurement of the pKa of racemic tetramethoxyresorcin[4]arenes explains the failure to obtain good yields in attempted Mannich reactions of these substrates under classical reaction conditions. The failure is related to the lack of adequate concentrations of the iminium ions that results from the reduced acid strength of tetraalkoxyresorcin[4]arenes compared with that of the parent octahydroxyresorcin[4]arenes. However, the preparation of a series of Mannich bases derived from racemic tetraalkoxyresorcin[4]arenes was accomplished under microwave-assisted aprotic reaction conditions and the use of preformed iminium ion intermediates. When the reactions were carried out with the use of chiral bis(aminol) ethers, mixtures of diastereomers were obtained that could be separated by flash chromatography. The absolute configurations of the enantiomerically pure tetrabenzoxazine derivatives were established in some cases by X-ray crystallographic analysis and by a comparison of the nuclear magnetic resonance spectroscopic data. The alkylation of racemic tetramethoxyresorcin[4]arenes was achieved with the use of an excess of 2-bromo-N-[(R)-(+)-(a-methylbenzyl)] acetamide in acetonitrile containing potassium carbonate. Enantioselective ligand-assisted reactions of aromatic aldehydes are also reported with the use of dialkylzinc reagents both in the absence and in the presence of terminal alkynes.

dc.publisherWiley-VCH Verlag GMBH
dc.subjectChiral auxiliaries
dc.subject- Resorcinarenes
dc.subjectAxial chirality
dc.subjectMannich reactions
dc.subjectConfiguration determination
dc.titleMannich and O-Alkylation Reactions of Tetraalkoxyresorcin[4]arenes. The Use of Some Products in Ligand-Assisted Reactions
dc.typeJournal Article
dcterms.source.titleEuropean Journal of Organic Chemistry

2007 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim


Please refer to the publisher for the definitive version.


as the corrected version (Volume 2007, Issue 7 , Pages 1203 - 1203)

curtin.departmentNanochemistry Research Institute, Curtin University of Technology
curtin.accessStatusFulltext not available
curtin.facultyResearch Centres
curtin.facultyCentre for Applied Organic Geochemistry
curtin.facultyCentres of Excellence

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