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NHC-catalysed enantioselectiveintramolecular formal [4+2] cycloadditions using carboxylic acids as azolium enolate precursors
Item metadata
dc.contributor.author | Attaba, Nassilia | |
dc.contributor.author | Smith, Andrew D. | |
dc.date.accessioned | 2020-12-07T15:55:02Z | |
dc.date.available | 2020-12-07T15:55:02Z | |
dc.date.issued | 2019-12-06 | |
dc.identifier | 263616613 | |
dc.identifier | a6cc809a-706f-4f16-84d9-2f51b04bb9dc | |
dc.identifier | 85077365416 | |
dc.identifier | 000512218000003 | |
dc.identifier.citation | Attaba , N & Smith , A D 2019 , ' NHC-catalysed enantioselectiveintramolecular formal [4+2] cycloadditions using carboxylic acids as azolium enolate precursors ' , Tetrahedron , vol. In press . https://doi.org/10.1016/j.tet.2019.130835 | en |
dc.identifier.issn | 0040-4020 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/66069881 | |
dc.identifier.uri | https://hdl.handle.net/10023/21074 | |
dc.description | We thank the European Research Council under the European Union's Seventh Framework Programme (FP7/2007-2013) ERC grant agreement no 279850 (NA) and the Royal Society (Wolfson Merit Award to ADS). | en |
dc.description.abstract | An NHC-catalysed intramolecular formal [4 + 2] cycloaddition protocol using carboxylic acid starting materials containing a tethered enone is reported. Optimisation studies using a model substrate showed that the use of the Yamaguchi reagent (2,4,6-trichlorobenzoyl chloride) for in situ preparation of a mixed anhydride was necessary for effective catalysis, leading to highest product yield and stereoselectivity. Using this protocol, a range of dihydrobenzofurans were accessed in moderate to high yield, and with high to excellent diastereo- and enantioselectivity (up to > 95:5 dr and > 99:1 er). This methodology was extended to the synthesis of syn-dihydrochromenone and syn-dihydropyranone derivatives in moderate to high yield and with excellent diastereo- and enantioselectivity. | |
dc.format.extent | 765470 | |
dc.language.iso | eng | |
dc.relation.ispartof | Tetrahedron | en |
dc.subject | NHC | en |
dc.subject | Enantioselective catalysis | en |
dc.subject | [4+2] cycloaddition | en |
dc.subject | Carboxylic acid | en |
dc.subject | Yamaguchi reagent | en |
dc.subject | QD Chemistry | en |
dc.subject | NDAS | en |
dc.subject.lcc | QD | en |
dc.title | NHC-catalysed enantioselectiveintramolecular formal [4+2] cycloadditions using carboxylic acids as azolium enolate precursors | en |
dc.type | Journal article | en |
dc.contributor.sponsor | European Commission | en |
dc.contributor.sponsor | The Royal Society | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | 10.1016/j.tet.2019.130835 | |
dc.description.status | Peer reviewed | en |
dc.date.embargoedUntil | 2020-12-06 | |
dc.identifier.grantnumber | N/A | en |
dc.identifier.grantnumber | WM140071 | en |
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