Transition-Metal-Catalyzed C-C and C-X Bond-Forming Reactions Using Cyclopropanols

Due to their high strain, unique bonding and relative ease of ring-cleavage, and because they are readily accessible, cyclopropanols have been employed in an increasing number of transition-metal-catalyzed C-C and C-X (X= heteroatom) bond-forming reactions. We review the recent literature and organize all the methods developed along mechanistic lines. 1 Introduction and Scope 2 C-C Bond Formation via Catalytic Generation and Coupling of Cyclopropanol-Derived Homoenolates 3 C-N Bond Formation via Catalytic Generation and Coupling of Cyclopropanol-Derived Homoenolates 4 C-C Bond Formation via Stoichiometric Generation and Coupling of Cyclopropanol-Derived Homoenolates 5 Ring Expansion of Cyclopropanols to Cyclobutanones via Transition-Metal-Catalyzed Wagner-Meerwein Shift 6 Transition-Metal-Catalyzed Rearrangement of Cyclopropanols to Cyclopentenones and Cyclohexenones 7 Synthesis of Medium-Size Rings via Multicomponent Reactions Involving Cyclopropanols 8 C-C and C-X Bond Formation via Free-Radical Fragmentation of Cyclopropanols 9 Summary and Outlook