Exploring the scope of asymmetric synthesis of β-Hydroxy-γ-lactams via Noyori-type reductions

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dc.contributor.author Lynch, Denis
dc.contributor.author Deasy, Rebecca E.
dc.contributor.author Clarke, Leslie-Ann
dc.contributor.author Slattery, Catherine N.
dc.contributor.author Khandavilli, Udaya Bhaskara Rao
dc.contributor.author Lawrence, Simon E.
dc.contributor.author Maguire, Anita R.
dc.contributor.author Magnus, Nicholas A.
dc.contributor.author Moynihan, Humphrey A.
dc.date.accessioned 2016-12-01T10:15:32Z
dc.date.available 2016-12-01T10:15:32Z
dc.date.issued 2016-09-22
dc.identifier.citation Lynch, D., Deasy, R. E., Clarke, L.-A., Slattery, C. N., Khandavilli, U. B. R., Lawrence, S. E., Maguire, A. R., Magnus, N. A. & Moynihan, H. A. (2016) ‘Exploring the scope of asymmetric synthesis of β-Hydroxy-γ-lactams via Noyori-type reductions, Organic Letters, 18, 4978-4981. doi: 10.1021/acs.orglett.6b02416 en
dc.identifier.volume 18 en
dc.identifier.startpage 4978 en
dc.identifier.endpage 4981 en
dc.identifier.issn 1523-7060
dc.identifier.uri http://hdl.handle.net/10468/3333
dc.identifier.doi 10.1021/acs.orglett.6b02416
dc.description.abstract Enantio- and diastereoselective hydrogenation of β-keto-γ-lactams with a ruthenium–BINAP catalyst, involving dynamic kinetic resolution, has been employed to provide a general, asymmetric approach to β-hydroxy-γ-lactams, a structural motif common to several bioactive compounds. Full conversion to the desired β-hydroxy-γ-lactams was achieved with high diastereoselectivity (up to >98% de) by addition of catalytic HCl and LiCl, while β-branching of the ketone substituent demonstrated a pronounced effect on the modest to excellent enantioselectivity (up to 97% ee) obtained. en
dc.description.sponsorship Enterprise Ireland (IP/2011/0097) en
dc.format.mimetype application/pdf en
dc.language.iso en en
dc.publisher American Chemical Society en
dc.rights © 2016 American Chemical Society. This document is the Accepted Manuscript version of a Published Work that appeared in final form in Organic Letters, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/acs.orglett.6b02416 en
dc.subject Serotonin en
dc.subject Acid en
dc.subject Beta-branching en
dc.title Exploring the scope of asymmetric synthesis of β-Hydroxy-γ-lactams via Noyori-type reductions en
dc.type Article (peer-reviewed) en
dc.internal.authorcontactother Denis Lynch, Abcrf, University College Cork, Cork, Ireland. +353-21-490-3000 Email: denis.lynch@ucc.ie en
dc.internal.availability Full text available en
dc.date.updated 2016-11-24T19:40:48Z
dc.description.version Accepted Version en
dc.internal.rssid 372344264
dc.internal.wokid 000385053900057
dc.contributor.funder Enterprise Ireland en
dc.contributor.funder Eli Lilly and Company en
dc.description.status Peer reviewed en
dc.identifier.journaltitle Organic letters en
dc.internal.copyrightchecked No !!CORA!! en
dc.internal.licenseacceptance Yes en
dc.internal.IRISemailaddress denis.lynch@ucc.ie en
dc.internal.IRISemailaddress simon.lawrence@ucc.ie en


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