Transition metal-catalyzed enantioselective ring-opening reactions of oxabicyclic alkenes.
Over the past five years, several metal-catalyzed asymmetric ring-cleaving reactions have been developed that generate ring-opened products in high yield and enantiomeric excess. These reactions can be carried out with a range of nucleophiles including hydride, stabilized and nonstabilized carbanions, alcohols, amines, and carboxylates. To achieve these results, three different transition metals have been employed, namely nickel, palladium, and rhodium, leading not only to synthetically useful transformations but also to a greater understanding of the reaction manifolds possible with these metals. This Account covers the work by our group and by others toward the development of new metal-catalyzed asymmetric ring-opening reactions of oxabicyclic alkenes.
Lautens
Mark
M
Davenport Research Laboratories, Department of Chemistry, University of Toronto, 80 St. George Street, Toronto, M5S 3H6 Canada.
Fagnou
Keith
K
Hiebert
Sheldon
S