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Diastereoselective and branched-aldehyde-selective tandem hydroformylation-hemiaminal formation : synthesis of functionalized piperidines and amino-alcohols

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dc.contributor.authorPittaway, Rachael
dc.contributor.authorFuentes, José A.
dc.contributor.authorClarke, Matthew L.
dc.date.accessioned2018-05-17T23:33:08Z
dc.date.available2018-05-17T23:33:08Z
dc.date.issued2017-06-02
dc.identifier.citationPittaway , R , Fuentes , J A & Clarke , M L 2017 , ' Diastereoselective and branched-aldehyde-selective tandem hydroformylation-hemiaminal formation : synthesis of functionalized piperidines and amino-alcohols ' , Organic Letters , vol. 19 , no. 11 , pp. 2845-2848 . https://doi.org/10.1021/acs.orglett.7b01049en
dc.identifier.issn1523-7060
dc.identifier.otherPURE: 249994299
dc.identifier.otherPURE UUID: 73218e5d-e264-4538-b81b-000c9d2198f2
dc.identifier.otherScopus: 85020003310
dc.identifier.otherORCID: /0000-0002-2444-1244/work/59464608
dc.identifier.otherWOS: 000402850900018
dc.identifier.urihttp://hdl.handle.net/10023/13388
dc.descriptionFinancial support by EPSRC DTG grant and EP/M0038868/1 is gratefully acknowledged.en
dc.description.abstractStarting from readily available allylglycine, a tandem hydroformylation–hemiaminal formation reaction has been developed for the synthesis of chiral functionalized piperidines, with very good diastereoselectivity and branched regioselectivity using Rh/(S,S,S)-BOBPHOS catalysts. Tandem hydroformylation–hemiacetal formation also proceeds with good diastereoselectivity (88:12), with the hemiacetal product being hydrogenated with retention of stereochemistry to give a chiral intermediate used in the synthesis of the new antibiotic nemonoxacin.
dc.format.extent4
dc.language.isoeng
dc.relation.ispartofOrganic Lettersen
dc.rightsCopyright © 2017 American Chemical Society. This work has been made available online in accordance with the publisher’s policies. This is the author created accepted version manuscript following peer review and as such may differ slightly from the final published version. The final published version of this work is available at: https://doi.org/10.1021/acs.orglett.7b01049en
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleDiastereoselective and branched-aldehyde-selective tandem hydroformylation-hemiaminal formation : synthesis of functionalized piperidines and amino-alcoholsen
dc.typeJournal articleen
dc.description.versionPostprinten
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.contributor.institutionUniversity of St Andrews.EaSTCHEMen
dc.identifier.doihttps://doi.org/10.1021/acs.orglett.7b01049
dc.description.statusPeer revieweden
dc.date.embargoedUntil2018-05-17


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