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

Abstract

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

Key words

cyclopropanol - ring strain - ring expansion - transition metals - total synthesis

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