Divergent Cascade Ring Expansion Reactions of Acryloyl Imides

Gideon James Grogan, Will Orukotan, Kleopas Palate, Balazs Pogranyi, Ryan Epton, Lee Duff, A.C. Whitwood, Jason Martin Lynam, William Paul Unsworth, Philipp Bobinski

Research output: Contribution to journalArticlepeer-review


Macrocyclic and medium-sized ring ketones, lactones and
lactams can all be made from common acryloyl imide starting
materials via divergent, one-pot cascade ring expansion reactions. Following either conjugate addition with an amine or nitromethane, or osmium(VIII) catalysed dihydoxylation, rearrangement via a 4-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, 3- or 4-atom ring expansion can be performed selectively, depending on whether the reaction is under kinetic or thermodynamic control.
Original languageEnglish
Article numbere202303270
JournalChemistry : A European Journal
Publication statusAccepted/In press - 21 Nov 2023

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