First asymmetric synthesis of trans-3,4-dimethyl-4-arylpiperidines

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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


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