Asymmetric 1,3-dipolar cycloadditions of acrylamides

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dc.contributor.author Kissane, Marie
dc.contributor.author Maguire, Anita R.
dc.date.accessioned 2012-05-23T09:55:42Z
dc.date.available 2012-05-23T09:55:42Z
dc.date.copyright 2009
dc.date.issued 2009
dc.identifier.citation KISSANE, M. & MAGUIRE, A. R. 2010. Asymmetric 1,3-dipolar cycloadditions of acrylamides. Chemical Society Reviews, 39, 845-883. doi:10.1039/B909358N en
dc.identifier.volume 39 en
dc.identifier.issued 2 en
dc.identifier.startpage 845 en
dc.identifier.endpage 883 en
dc.identifier.issn 0306-0012
dc.identifier.issn 1460-4744
dc.identifier.uri http://hdl.handle.net/10468/593
dc.identifier.doi 10.1039/B909358N
dc.description.abstract This critical review, which is relevant to researchers in synthetic organic chemistry, focuses on asymmetric 1,3-dipolar cycloadditions with acrylamides. The use of chiral acrylamides as dipolarophiles leads to high levels of stereocontrol, due to conformational constraint in the acrylamides. Employment of chiral tertiary acrylamides containing nitrogen heterocycles is particularly effective in controlling the stereoselectivity. Following a general overview of 1,3-dipolar cycloadditions, the main body of the review focuses on asymmetric 1,3-dipolar cycloadditions of acrylamides with nitrile oxides, nitrones, diazoalkanes and azomethine ylides, with particular emphasis on the rationale for the observed stereocontrol (215 references). en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher RSC Publishing en
dc.relation.uri http://pubs.rsc.org/en/content/articlelanding/2010/cs/b909358n
dc.rights ©2010, The Authors. Exclusive licence to publish RSC Publishing. en
dc.subject Asymmetric 1,3-dipolar cycloadditions en
dc.subject Chiral acrylamides en
dc.subject Stereocontrol en
dc.subject Regioselectivity en
dc.subject Nitrile oxides en
dc.subject Nitrones en
dc.subject Diazoalkanes en
dc.subject Azomethine ylides en
dc.subject Stereoselectivity en
dc.subject.lcsh Organic compounds--Synthesis en
dc.subject.lcsh Stereochemistry en
dc.title Asymmetric 1,3-dipolar cycloadditions of acrylamides en
dc.type Review en
dc.internal.authorurl http://publish.ucc.ie/researchprofiles/V001/amaguire en
dc.internal.authorcontactother Department of Chemistry & School of Pharmacy, Analytical and Biological Chemistry Research Facility, University College Cork, Cork, Ireland. T.: +353 (0)21 4901693 en
dc.internal.availability Full text available en
dc.description.version Accepted Version en
dc.internal.rssid 5956736
dc.description.status Peer reviewed en
dc.identifier.journaltitle Chemical Society Reviews en
dc.internal.copyrightchecked Checked policy on website: http://www.rsc.org/AboutUs/Copyright/Authordeposition.asp Allowed Deposition by the author(s) When the author accepts the exclusive Licence to Publish for a journal article, he/she retains certain rights concerning the deposition of the whole article. He/she may: •Deposit the accepted version of the submitted article in their institutional repository(ies). There shall be an embargo of making the above deposited material available to the public of 12 months from the date of acceptance. There shall be a link from this article to the PDF of the final published article on the RSC's website once this final version is available. en
dc.internal.IRISemailaddress a.maguire@ucc.ie en


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