Stereoselective, dual-mode ruthenium-catalyzed ring expansion of alkynylcyclopropanols.
A novel, dual-pathway ring expansion of alkynylcyclopropanols is described. On treatment with a ruthenium catalyst, these compounds undergo highly selective enlargement to either (Z)-alkylidene cyclobutanones or beta-substituted cyclopentenones. The unique ability to access the least selective double bond isomers of alkylidene cyclobutanones and the dramatic shift of reactivity observed further illustrate the particular intricacies of ruthenium catalysis when compared to other alkynophilic transition metals.
Trost
Barry M
BM
Department of Chemistry, Stanford University, Stanford, California 94305-5080, USA. bmtrost@stanford.edu
Xie
Jia
J
Maulide
Nuno
N
D000433:1-Propanol / Q000737:chemistry*; D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods*; D003503:Cyclobutanes / Q000737:chemistry; D004583:Electrons; D004988:Ethers, Cyclic / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008670:Metals; D008956:Models, Chemical; D012428:Ruthenium / Q000737:chemistry*
D003503:Cyclobutanes; D004988:Ethers, Cyclic; D008670:Metals; C538814:cyclobutanol; C043657:cyclopropanol; D012428:Ruthenium; D000433:1-Propanol