dc.contributor.author |
Jamieson, ML |
en |
dc.contributor.author |
Hume, Paul |
en |
dc.contributor.author |
Furkert, Daniel |
en |
dc.contributor.author |
Brimble, Margaret |
en |
dc.date.accessioned |
2016-07-25T03:09:08Z |
en |
dc.date.issued |
2016-02-05 |
en |
dc.identifier.citation |
Organic Letters, 2016, 18 (3), pp. 468 - 471 |
en |
dc.identifier.issn |
1523-7060 |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/29581 |
en |
dc.description.abstract |
Cobalt salts exert an unexpected and profound influence on the reactivity of epoxides with dimethylsulfoxonium methylide. In the presence of a cobalt catalyst, conditions for epoxide to an oxetane ring expansion instead deliver homoallylic alcohol products, corresponding to a two-carbon epoxide homologation/ring-opening tandem process. The observed reactivity change appears to be specifically due to cobalt salts and is broadly applicable to a variety of epoxides, retaining the initial stereochemistry. This transformation also provides operationally simple access to enantiopure homoallylic alcohols from chiral epoxides without use of organometallic reagents. Tandem epoxidation–homologation of aldehydes in a single step is also demonstrated. |
en |
dc.description.uri |
http://www.ncbi.nlm.nih.gov/pubmed/26829490 |
en |
dc.language |
English |
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/
http://pubs.acs.org/page/copyright/index.html |
en |
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
en |
dc.title |
Divergent Reactivity via Cobalt Catalysis: An Epoxide Olefination |
en |
dc.type |
Journal Article |
en |
dc.identifier.doi |
10.1021/acs.orglett.5b03514 |
en |
pubs.issue |
3 |
en |
pubs.begin-page |
468 |
en |
pubs.volume |
18 |
en |
dc.description.version |
VoR - Version of Record |
en |
dc.rights.holder |
|
en |
dc.identifier.pmid |
26829490 |
en |
pubs.author-url |
http://pubs.acs.org/doi/abs/10.1021/acs.orglett.5b03514 |
en |
pubs.end-page |
471 |
en |
pubs.publication-status |
Published |
en |
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
en |
pubs.subtype |
Article |
en |
pubs.elements-id |
520233 |
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 |
dc.identifier.eissn |
1523-7052 |
en |
pubs.record-created-at-source-date |
2016-07-04 |
en |
pubs.online-publication-date |
2016-01-27 |
en |
pubs.dimensions-id |
26829490 |
en |