Asymmetric Michael Addition of 2-Trimethylsilyloxyfuran 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 2011-09-19T01:54:53Z en
dc.date.issued 1998 en
dc.identifier.citation Tetrahedron Asymmetry 9 (7), 1257-1267, 1998 en
dc.identifier.issn 0957-4166 en
dc.identifier.uri http://hdl.handle.net/2292/8078 en
dc.description.abstract Asymmetric Michael reactions of 1,4-naphthoquinones bearing a chiral auxiliary at C-2 1-4 with 2-trimethylsilyloxyfuran using various Lewis acids afforded the corresponding furofuran adducts 5-12. Moderate levels of diastereomeric excess were obtained using (R)-pantolactone, (S)-N-methyl-2-hydroxysuccinimide and (R)-(+)-4-benzyl-2-oxazolidinone as chiral auxiliaries. Low asymmetric induction was achieved using a camphorsultam auxiliary. X-Ray crystallographic analysis of the pantolactone adduct enabled determination of the absolute stereochemistry of all adducts obtained. Evidence that the TMS-furan addition occurs via a Michael reaction rather than a Diels-Alder cycloaddition is provided. (C) 1998 Elsevier Science Ltd. All rights reserved. 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 DIELS-ALDER REACTIONS en
dc.subject ACID en
dc.subject ANTIBIOTICS en
dc.title Asymmetric Michael Addition of 2-Trimethylsilyloxyfuran to Chiral Naphthoquinones en
dc.type Journal Article en
dc.identifier.doi 10.1016/S0957-4166(98)00088-3 en
pubs.issue 7 en
pubs.begin-page 1257 en
pubs.volume 9 en
dc.rights.holder Copyright: 1998 Elsevier Science Ltd. en
pubs.end-page 1267 en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 33968 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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