Affiliation:
1. Department of Chemistry University of York York YO10 5DD UK
2. Organisch-Chemisches Institut Universität Heidelberg Im Neuenheimer Feld 270 69120 Heidelberg Germany
Abstract
AbstractMacrocyclic 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.
Funder
Royal Society
Studienstiftung des Deutschen Volkes
Subject
General Chemistry,Catalysis,Organic Chemistry