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Enantioselective synthesis in continuous flow : polymer supported isothiourea-catalyzed enantioselective Michael addition-cyclization with α-azol-2-ylacetophenones
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dc.contributor.author | Zhou, Zhanyu | |
dc.contributor.author | Kasten, Kevin | |
dc.contributor.author | Kang, Tengfei | |
dc.contributor.author | Cordes, David Bradford | |
dc.contributor.author | Smith, Andrew David | |
dc.date.accessioned | 2024-05-08T16:30:01Z | |
dc.date.available | 2024-05-08T16:30:01Z | |
dc.date.issued | 2024-05-17 | |
dc.identifier | 301377986 | |
dc.identifier | 0bed430f-bd4b-4a6c-8577-b6cf5592d346 | |
dc.identifier | 85192267540 | |
dc.identifier.citation | Zhou , Z , Kasten , K , Kang , T , Cordes , D B & Smith , A D 2024 , ' Enantioselective synthesis in continuous flow : polymer supported isothiourea-catalyzed enantioselective Michael addition-cyclization with α-azol-2-ylacetophenones ' , Organic Process Research & Development , vol. 28 , no. 5 , pp. 2041–2049 . https://doi.org/10.1021/acs.oprd.4c00113 | en |
dc.identifier.issn | 1083-6160 | |
dc.identifier.other | ORCID: /0000-0002-5366-9168/work/159433106 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/159433220 | |
dc.identifier.uri | https://hdl.handle.net/10023/29843 | |
dc.description | Engineering and Physical Sciences Research Council - EP/W007517, EP/T023643/1 | en |
dc.description.abstract | A packed reactor bed incorporating a polymer-supported isothiourea HyperBTM catalyst derivative has been used to promote the enantioselective synthesis of a range of heterocyclic products derived from α-azol-2-ylacetophenones and -acetamides combined with alkyl, aryl, and heterocyclic α,β-unsaturated homoanhydrides in continuous flow via an α,β-unsaturated acyl-ammonium intermediate. The products are generated in good to excellent yields and generally in excellent enantiopurity (up to 97:3 er). Scale-up is demonstrated on a 15 mmol scale, giving the heterocyclic product in 68% overall yield with 98:2 er after recrystallization. | |
dc.format.extent | 2017012 | |
dc.language.iso | eng | |
dc.relation.ispartof | Organic Process Research & Development | en |
dc.subject | DAS | en |
dc.title | Enantioselective synthesis in continuous flow : polymer supported isothiourea-catalyzed enantioselective Michael addition-cyclization with α-azol-2-ylacetophenones | en |
dc.type | Journal article | en |
dc.contributor.sponsor | UK Research and Innovation | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | EPSRC | en |
dc.contributor.sponsor | UK Research and Innovation | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | https://doi.org/10.1021/acs.oprd.4c00113 | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | EP/W007517/1 | en |
dc.identifier.grantnumber | EP/T023643/1 | en |
dc.identifier.grantnumber | EP/T023643/1 | en |
dc.identifier.grantnumber | EP/W007517/1 | en |
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