Show simple item record

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, Matthew
dc.contributor.authorMcKee, V.
dc.contributor.authorMcGrath, M.
dc.contributor.authorMocerino, Mauro
dc.contributor.authorPoulton, A.
dc.contributor.authorSampler, E.
dc.contributor.authorSkelton, B.
dc.contributor.authorWhite, A.
dc.date.accessioned2017-01-30T12:08:55Z
dc.date.available2017-01-30T12:08:55Z
dc.date.created2009-03-05T00:55:25Z
dc.date.issued2006
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: pp. 5117-5134.
dc.identifier.urihttp://hdl.handle.net/20.500.11937/18631
dc.identifier.doi10.1002/ejoc.200600590
dc.description.abstract

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-raycrystallographic 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.subjectDiastereoselectivity
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.volume2006
dcterms.source.startPage5117
dcterms.source.endPage5134
dcterms.source.issn1434193X
dcterms.source.titleEuropean Journal of Organic Chemistry
curtin.note

Copyright © 2006 John Wiley & Sons, Ltd.

curtin.departmentCentre for Applied Organic Geochemistry (COE )
curtin.accessStatusFulltext not available
curtin.facultyCentre for Applied Organic Geochemistry (COE)
curtin.facultyFaculty of Science and Engineering


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record