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Divergent Cascade Ring-Expansion Reactions of Acryloyl Imides.
Orukotan, Will E; Palate, Kleopas Y; Pogrányi, Balázs; Bobinski, Philipp; Epton, Ryan G; Duff, Lee; Whitwood, Adrian C; Grogan, Gideon; Lynam, Jason M; Unsworth, William P.
Afiliação
  • Orukotan WE; Department of Chemistry, University of York, York, YO10 5DD, UK.
  • Palate KY; Department of Chemistry, University of York, York, YO10 5DD, UK.
  • Pogrányi B; Department of Chemistry, University of York, York, YO10 5DD, UK.
  • Bobinski P; Organisch-Chemisches Institut, Universität Heidelberg, Im Neuenheimer Feld 270, 69120, Heidelberg, Germany.
  • Epton RG; Department of Chemistry, University of York, York, YO10 5DD, UK.
  • Duff L; Department of Chemistry, University of York, York, YO10 5DD, UK.
  • Whitwood AC; Department of Chemistry, University of York, York, YO10 5DD, UK.
  • Grogan G; Department of Chemistry, University of York, York, YO10 5DD, UK.
  • Lynam JM; Department of Chemistry, University of York, York, YO10 5DD, UK.
  • Unsworth WP; Department of Chemistry, University of York, York, YO10 5DD, UK.
Chemistry ; 30(8): e202303270, 2024 Feb 07.
Article em En | MEDLINE | ID: mdl-37987097
Macrocyclic and medium-sized ring ketones, lactones and lactams can all be made from common acryloyl imide starting materials through divergent, one-pot cascade ring-expansion reactions. Following either conjugate addition with an amine or nitromethane, or osmium(VIII)-catalysed dihydoxylation, rearrangement through a four-atom ring expansion takes place spontaneously to form the ring expanded products. A second ring expansion can also be performed following a second iteration of imide formation and alkene functionalisation/ring expansion. In the dihydroxylation series, three- or four-atom ring expansion can be performed selectively, depending on whether the reaction is under kinetic or thermodynamic control.
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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2024 Tipo de documento: Article

Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2024 Tipo de documento: Article