Asymmetric Diels-Alder Addition of Cyclopentadiene to Chiral Naphthoquinones

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dc.contributor.author Brimble, Margaret en
dc.contributor.author Mcewan, JF en
dc.contributor.author Murray, Pamela en
dc.date.accessioned 2011-09-19T01:54:22Z en
dc.date.issued 1998 en
dc.identifier.citation Tetrahedron Asymmetry 9 (7), 1239-1255, 1998 en
dc.identifier.issn 0957-4166 en
dc.identifier.uri http://hdl.handle.net/2292/8076 en
dc.description.abstract Diels-Alder reactions of 1,4-naphthoquinones bearing a chiral auxiliary at C-2, with cyclopentadiene under Lewis acid conditions afforded the corresponding Diels-Alder. adducts. High levels of diastereomeric excess were obtained using (R)-pantolactone, (S)-N-methyl-2-hydroxysuccinimide and trans-2-phenylcyclohexanol as auxiliaries. Moderate asymmetric induction was achieved using Oppolzer's camphorsultam and (R)-(+)-4-benzyl-2-oxazolidinone as auxiliaries. X-Ray crystallographic analysis of the pantolactone adduct enabled determination of the stereochemistry of all adducts obtained. en
dc.language EN en
dc.relation.ispartofseries Tetrahedron-Asymmetry en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/0957-4166/ en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.subject LEWIS ACID en
dc.subject CYCLOADDITIONS en
dc.subject INDUCTION en
dc.subject REAGENTS en
dc.subject MODEL en
dc.title Asymmetric Diels-Alder Addition of Cyclopentadiene to Chiral Naphthoquinones en
dc.type Journal Article en
dc.identifier.doi 10.1016/S0957-4166(98)00087-1 en
pubs.issue 7 en
pubs.begin-page 1239 en
pubs.volume 9 en
dc.rights.holder Copyright: 1998 Elsevier Science Ltd. en
pubs.end-page 1255 en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 33974 en
pubs.org-id Science en
pubs.org-id Chemistry en
pubs.org-id Science Research en
pubs.org-id Maurice Wilkins Centre (2010-2014) en
pubs.record-created-at-source-date 2010-09-01 en


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