dc.contributor.author |
Hung, KY |
en |
dc.contributor.author |
Harris, Paul |
en |
dc.contributor.author |
Brimble, Margaret |
en |
dc.coverage.spatial |
United States |
en |
dc.date.accessioned |
2011-09-18T21:37:32Z |
en |
dc.date.issued |
2010 |
en |
dc.identifier.citation |
J Org Chem 75(24):8728-8731 17 Dec 2010 |
en |
dc.identifier.issn |
0022-3263 |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/7979 |
en |
dc.description.abstract |
An efficient stereoselective synthesis of fully protected (2S,4R)-4-methylpipecolic acid has been developed. The synthesis was achieved by initial asymmetric α-alkylation of glycine with a chiral iodide, affording the linear precursor as a single stereoisomer. Subsequent aldehyde formation using OsO(4)/NaIO(4) followed by immediate intramolecular cyclization afforded an enamine that was then subjected to hydrogenation to give the final compound in 23% yield over 10 steps. |
en |
dc.language |
eng |
en |
dc.publisher |
The American Chemical Society |
en |
dc.relation.ispartofseries |
J. Org. Chem. |
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/0022-3263/ |
en |
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
en |
dc.subject |
Alkylation |
en |
dc.subject |
Cyclization |
en |
dc.subject |
Hydrogenation |
en |
dc.subject |
Molecular Structure |
en |
dc.subject |
Pipecolic Acids |
en |
dc.subject |
Stereoisomerism |
en |
dc.title |
Synthesis of methyl N-Boc-(2S,4R)-4-methylpipecolate. |
en |
dc.type |
Journal Article |
en |
dc.identifier.doi |
10.1021/jo102038q |
en |
pubs.issue |
24 |
en |
pubs.begin-page |
8728 |
en |
pubs.volume |
75 |
en |
dc.rights.holder |
Copyright: 2010 American Chemical Society |
en |
dc.identifier.pmid |
21090804 |
en |
pubs.end-page |
8731 |
en |
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
en |
pubs.subtype |
Article |
en |
pubs.elements-id |
190926 |
en |
pubs.org-id |
Science |
en |
pubs.org-id |
Biological Sciences |
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 |
2011-06-30 |
en |
pubs.dimensions-id |
21090804 |
en |