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Probing regio- and enantioselectivity in the formal [2+2] cycloaddition of C(1)-alkyl ammonium enolates with - and ,-substituted tri-fluoromethylenones
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dc.contributor.author | Wang, Yihong | |
dc.contributor.author | Young, Claire Mary | |
dc.contributor.author | Cordes, David Bradford | |
dc.contributor.author | Slawin, Alexandra Martha Zoya | |
dc.contributor.author | Smith, Andrew David | |
dc.date.accessioned | 2023-05-15T15:30:07Z | |
dc.date.available | 2023-05-15T15:30:07Z | |
dc.date.issued | 2023-06-16 | |
dc.identifier.citation | Wang , Y , Young , C M , Cordes , D B , Slawin , A M Z & Smith , A D 2023 , ' Probing regio- and enantioselectivity in the formal [2+2] cycloaddition of C(1)-alkyl ammonium enolates with - and ,-substituted tri-fluoromethylenones ' , The Journal of Organic Chemistry , vol. 88 , no. 12 , pp. 7784-7799 . https://doi.org/10.1021/acs.joc.2c02688 | en |
dc.identifier.issn | 0022-3263 | |
dc.identifier.other | PURE: 284268463 | |
dc.identifier.other | PURE UUID: 3bdec19d-04c5-4540-a70a-4045b87ceebe | |
dc.identifier.other | ORCID: /0000-0002-9527-6418/work/135454835 | |
dc.identifier.other | ORCID: /0000-0002-5366-9168/work/135454902 | |
dc.identifier.other | ORCID: /0000-0002-2104-7313/work/135455053 | |
dc.identifier.other | Scopus: 85161052597 | |
dc.identifier.uri | https://hdl.handle.net/10023/27618 | |
dc.description | Funding: UK Engineering and Physical Sciences Research Council - EP/S019359/1; China Scholarship Council. | en |
dc.description.abstract | The isothiourea-catalyzed regio- and enantioselective formal [2 + 2] cycloaddition of C(1)-alkyl and C(1)-unsubstituted ammonium enolates with β- and α,β-substituted trifluoromethylenones has been developed. In all cases, preferential [2 + 2]-cycloaddition over the alternative [4 + 2]-cycloaddition is observed, giving β-lactones with excellent diastereo- and enantioselectivity (34 examples, up to >95:5 dr, >99:1 er). The regioselectivity of the process was dictated by the nature of the substituents on both reaction components. Solely [2 + 2] cycloaddition products are observed when using α,β-substituted trifluoromethylenones or α-trialkylsilyl acetic acid derivatives; both [2 + 2] and [4 + 2] cycloaddition products are observed when using β-substituted trifluoromethylenones and α-alkyl-α-trialkylsilyl acetic acids as reactants, with the [2 + 2] cycloaddition as the major reaction product. The beneficial role of the α-silyl substituent within the acid component in this protocol has been demonstrated by control experiments. | |
dc.format.extent | 16 | |
dc.language.iso | eng | |
dc.relation.ispartof | The Journal of Organic Chemistry | en |
dc.rights | Copyright © 2023 The Authors. Published by American Chemical Society under CC BY. | en |
dc.subject | QD Chemistry | en |
dc.subject | DAS | en |
dc.subject | MCC | en |
dc.subject.lcc | QD | en |
dc.title | Probing regio- and enantioselectivity in the formal [2+2] cycloaddition of C(1)-alkyl ammonium enolates with - and ,-substituted tri-fluoromethylenones | en |
dc.type | Journal article | en |
dc.contributor.sponsor | EPSRC | en |
dc.description.version | Publisher PDF | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.contributor.institution | University of St Andrews. Institute of Behavioural and Neural Sciences | en |
dc.identifier.doi | https://doi.org/10.1021/acs.joc.2c02688 | |
dc.description.status | Peer reviewed | en |
dc.identifier.grantnumber | EP/S019359 | en |
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