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Exploring chemical diversity via a modular reaction pairing strategy

dc.contributor.authorLoh, Joanna K.
dc.contributor.authorYoon, Sun Young
dc.contributor.authorSamarakoon, Thiwanka Bandara
dc.contributor.authorRolfe, Alan
dc.contributor.authorPorubsky, Patrick R.
dc.contributor.authorNeuenswander, Benjamin
dc.contributor.authorLushington, Gerald H.
dc.contributor.authorHanson, Paul R.
dc.date.accessioned2014-04-17T21:03:56Z
dc.date.available2014-04-17T21:03:56Z
dc.date.issued2012-08-15
dc.identifier.citationLoh, Joanna K, Sun Young Yoon, Thiwanka B Samarakoon, Alan Rolfe, Patrick Porubsky, Benjamin Neuenswander, Gerald H Lushington, and Paul R Hanson. 2012. “Exploring Chemical Diversity via a Modular Reaction Pairing Strategy.” Beilstein Journal of Organic Chemistry 8 : 1293–1302. http://dx.doi.org/10.3762/bjoc.8.147
dc.identifier.urihttp://hdl.handle.net/1808/13546
dc.description.abstractThe efficient synthesis of an 80-member library of unique benzoxathiazocine 1,1-dioxides by a microwave-assisted, intermolecular nucleophilic aromatic substitution (SNAr) diversification pathway is reported. Eight benzofused sultam cores were generated by means of a sulfonylation/SNAr/Mitsunobu reaction pairing protocol, and subsequently diversified by intermolecular SNAr with ten chiral, non-racemic amine/amino alcohol building blocks. Computational analyses were employed to explore and evaluate the chemical diversity of the library.
dc.description.sponsorshipFinancial support of this work was provided by the National Institute of General Medical Sciences and is gratefully acknowledged (P50-GM069663 and P41-GM076302). In addition, funding from The University of Kansas for an Undergraduate Research Award (S.Y.) is gratefully acknowledged.
dc.publisherBeilstein-Institut
dc.rightsThis is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)
dc.rights.urihttp://creativecommons.org/licenses/by/2.0
dc.subjectBenzoxathiazocine 1
dc.subject1- Dioxides
dc.subjectChemical Diversity
dc.subjectInformatics
dc.subjectNucleophilic Aromatic Substitution
dc.subjectSultams
dc.titleExploring chemical diversity via a modular reaction pairing strategy
dc.typeArticle
kusw.kuauthorLoh, Joanna K.
kusw.kuauthorYoon, Sung Young
kusw.kuauthorSamarakoon, Thiwanka B.
kusw.kuauthorRolfe, Alan
kusw.kuauthorPorubsky, Patrick
kusw.kuauthorNeuenswander, Benjamin
kusw.kuauthorLushington, Gerald H.
kusw.kuauthorHanson, Paul R.
kusw.kudepartmentDepartment of Chemisty
kusw.oastatusfullparticipation
dc.identifier.doi10.3762/bjoc.8.147
kusw.oaversionScholarly/refereed, publisher version
kusw.oapolicyThis item meets KU Open Access policy criteria.
dc.rights.accessrightsopenAccess


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This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)
Except where otherwise noted, this item's license is described as: This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (http://www.beilstein-journals.org/bjoc)