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 |