dc.contributor.author |
Furkert, Daniel |
en |
dc.contributor.author |
Husbands, SM |
en |
dc.date.accessioned |
2012-03-11T22:48:32Z |
en |
dc.date.issued |
2007-09-13 |
en |
dc.identifier.citation |
Organic Letters 9(19):3769-3771 13 Sep 2007 |
en |
dc.identifier.issn |
1523-7060 |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/13737 |
en |
dc.description.abstract |
The first asymmetric synthesis of the trans-3,4-dimethyl-4-arylpiperidine opioid antagonist scaffold is reported. C-3 stereochemistry was established via CBS reduction and stereoselective anti-S_{N}2‘ cuprate displacement of the derived allylic phosphonate. The resultant vinyl bromide was then elaborated to the target compound by Suzuki coupling and trans-selective 4-methylation. Extension of this methodology should allow general enantioselective access to highly substituted piperidine ring systems. |
en |
dc.language |
EN |
en |
dc.publisher |
American Chemical Society |
en |
dc.relation.ispartofseries |
Organic Letters |
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/1523-7060/ |
en |
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
en |
dc.subject |
DERIVATIVES |
en |
dc.subject |
ANTAGONISTS |
en |
dc.subject |
ALKYLATION |
en |
dc.subject |
POTENT |
en |
dc.title |
First asymmetric synthesis of trans-3,4-dimethyl-4-arylpiperidines |
en |
dc.type |
Journal Article |
en |
dc.identifier.doi |
10.1021/ol0713988 |
en |
pubs.issue |
19 |
en |
pubs.begin-page |
3769 |
en |
pubs.volume |
9 |
en |
dc.rights.holder |
Copyright: American Chemical Society |
en |
dc.identifier.pmid |
17711289 |
en |
pubs.end-page |
3771 |
en |
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
en |
pubs.subtype |
Article |
en |
pubs.elements-id |
114100 |
en |
pubs.org-id |
Science |
en |
pubs.org-id |
Chemistry |
en |
pubs.record-created-at-source-date |
2012-02-16 |
en |
pubs.dimensions-id |
17711289 |
en |