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 |