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Isothiourea-catalyzed functionalization of pyrrolyl- and indolylacetic acid : enantioselective synthesis of dihydropyridinones and one-pot synthesis of pyridinones
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dc.contributor.author | Zhang, Shuyue | |
dc.contributor.author | Bacheley, Lucas | |
dc.contributor.author | Young, Claire Mary | |
dc.contributor.author | Stark, Daniel Graham | |
dc.contributor.author | O'Riordan, Timothy | |
dc.contributor.author | Slawin, Alexandra Martha Zoya | |
dc.contributor.author | Smith, Andrew David | |
dc.date.accessioned | 2020-10-09T14:30:01Z | |
dc.date.available | 2020-10-09T14:30:01Z | |
dc.date.issued | 2020-10 | |
dc.identifier | 268542463 | |
dc.identifier | a113b3cf-7b58-4778-9a72-cfe240fcf546 | |
dc.identifier | 000546624300001 | |
dc.identifier | 85087709766 | |
dc.identifier.citation | Zhang , S , Bacheley , L , Young , C M , Stark , D G , O'Riordan , T , Slawin , A M Z & Smith , A D 2020 , ' Isothiourea-catalyzed functionalization of pyrrolyl- and indolylacetic acid : enantioselective synthesis of dihydropyridinones and one-pot synthesis of pyridinones ' , Asian Journal of Organic Chemistry , vol. 9 , no. 10 , pp. 1562-1566 . https://doi.org/10.1002/ajoc.202000290 | en |
dc.identifier.issn | 2193-5815 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/77131143 | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/77131207 | |
dc.identifier.uri | https://hdl.handle.net/10023/20754 | |
dc.description | Funding: ERC under the European Union's Seventh Framework Programme (FP7/2007–2013) / ERC grant agreement no 279850. We thank Syngenta and EPSRC grant No. EP/K503162/1 (DGS), ADS thanks the Royal Society for a Wolfson Research Merit Award. | en |
dc.description.abstract | A protocol for the isothiourea‐catalyzed enantioselective functionalization of pyrrolyl‐ and indolylacetic acids has been developed. Stereodefined dihydropyridinones are accessed through formal [4+2] cycloaddition of an in situ generated isothiouronium enolate with α,β‐unsaturated ketimines. The dihydropyridinones are obtained in moderate to excellent yield (26–97%), excellent diastereocontrol (all >95 : 5 dr) and moderate to excellent enantiocontrol (75 : 25–99 : 1 er). An unusual elimination of pyrrole or indole from the dihydropyridinone to access achiral pyridinones was observed and could be selectively promoted. A further one‐pot synthesis using an acyl imidazole was developed to give pyridinones in good to excellent yields (67–91%). | |
dc.format.extent | 5 | |
dc.format.extent | 4215510 | |
dc.language.iso | eng | |
dc.relation.ispartof | Asian Journal of Organic Chemistry | en |
dc.subject | Heterocycle synthesis | en |
dc.subject | Organocatalysis | en |
dc.subject | Pyrrole elimination | en |
dc.subject | Indole elimination | en |
dc.subject | Isothiourea | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject.lcc | QD | en |
dc.title | Isothiourea-catalyzed functionalization of pyrrolyl- and indolylacetic acid : enantioselective synthesis of dihydropyridinones and one-pot synthesis of pyridinones | 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. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.identifier.doi | 10.1002/ajoc.202000290 | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | N/A | en |
dc.identifier.grantnumber | WM140071 | en |
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