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Non-bonding 1,5-S•••O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles
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dc.contributor.author | Robinson, Emily R. T. | |
dc.contributor.author | Walden, Daniel M. | |
dc.contributor.author | Fallan, Charlene | |
dc.contributor.author | Greenhalgh, Mark D. | |
dc.contributor.author | Cheong, Paul Ha-Yeon | |
dc.contributor.author | Smith, Andrew D. | |
dc.date.accessioned | 2016-08-03T11:30:05Z | |
dc.date.available | 2016-08-03T11:30:05Z | |
dc.date.issued | 2016-12-01 | |
dc.identifier | 244263232 | |
dc.identifier | 9dffa39d-0ff3-4a5a-9227-6987ea806800 | |
dc.identifier | 84995687647 | |
dc.identifier | 000391453200006 | |
dc.identifier.citation | Robinson , E R T , Walden , D M , Fallan , C , Greenhalgh , M D , Cheong , P H-Y & Smith , A D 2016 , ' Non-bonding 1,5-S•••O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles ' , Chemical Science , vol. 7 , no. 12 , pp. 6919-6927 . https://doi.org/10.1039/C6SC00940A | en |
dc.identifier.issn | 2041-6520 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/36567483 | |
dc.identifier.uri | https://hdl.handle.net/10023/9248 | |
dc.description | We thank the Royal Society (URF to ADS), the EPSRC (ERTR – grant code EP/J500549/1) and the European Research Council under the European Union’s Seventh Framework Programme (FP7/2007-2013) ERC grant agreement n° 279850 (CF). We also thank the EPSRC UK National Mass Spectrometry Facility at Swansea University. PHYC is the Vicki & Patrick F. Stone Scholar of Oregon State University and gratefully acknowledges financial support from the Stone Family & the National Science Foundation (NSF, CHE-1352663), and the computing infrastructure in part provided by the NSF Phase-2 CCI, Center for Sustainable Materials Chemistry (NSF CHE-1102637). DMW also acknowledges financial support from the Johnson Research Fellowship. | en |
dc.description.abstract | Isothiourea-catalyzed annulations between 2-acyl benzazoles and α,β-unsaturated acyl ammonium intermediates are selectively tuned to form either lactam or lactone heterocycles in good yields (up to 95%) and high ee (up to 99%) using benzothiazole or benzoxazole derivatives, respectively. Computation gives insight into the significant role of two 1,5-S•••O interactions in controlling the structural preorganization and chemoselectivity observed within the lactam synthesis with benzothiazoles as nucleophiles. When using benzazoles the absence of a second stabilizing non-bonding 1,5-S•••O interaction leads to a dominant CH•••O interaction in determining structural preorganization and lactone formation. | |
dc.format.extent | 9 | |
dc.format.extent | 1571096 | |
dc.language.iso | eng | |
dc.relation.ispartof | Chemical Science | en |
dc.subject | QD Chemistry | en |
dc.subject | NDAS | en |
dc.subject.lcc | QD | en |
dc.title | Non-bonding 1,5-S•••O interactions govern chemo- and enantioselectivity in isothiourea-catalyzed annulations of benzazoles | en |
dc.type | Journal article | en |
dc.contributor.sponsor | The Royal Society | en |
dc.contributor.sponsor | European Commission | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. Biomedical Sciences Research Complex | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | 10.1039/C6SC00940A | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | UF090013 | en |
dc.identifier.grantnumber | N/A | en |
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