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- Title
Divergent Cascade Ring-Expansion Reactions of Acryloyl Imides.
- Authors
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
- Abstract
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.
- Publication
Chemistry (Weinheim an der Bergstrasse, Germany), 2024, Vol 30, Issue 8, pe202303270
- ISSN
1521-3765
- Publication type
Journal Article
- DOI
10.1002/chem.202303270