Abstract
Developments in the synthesis of bicyclo[n.1.0]alkanes by lithium 2,2,6,6-tetramethylpiperidide-induced intramolecular cyclopropanation of unsaturated terminal epoxides are reviewed. The main alternative intramolecular cyclopropanation strategies are also briefly discussed to put the epoxide chemistry in perspective. Terminal epoxide (or chlorohydrin) precursors possessing a tethered alkene undergo intramolecular cyclopropanation with complete stereoselectivity and in generally good to excellent yields to give cyclopropyl alcohols; application of this cyclopropanation methodology in the synthesis of natural products is also reviewed.
Keywords: Cyclopropanes, epoxide, intramolecular cyclopropanation, lithium 2, 2, 6, 6-tetramethylpiperidide, total synthesis.
Graphical Abstract
Call for Papers in Thematic Issues
Catalytic C-H bond activation as a tool for functionalization of heterocycles
The major topic is the functionalization of heterocycles through catalyzed C-H bond activation. The strategies based on C-H activation not only provide straightforward formation of C-C or C-X bonds but, more importantly, allow for the avoidance of pre-functionalization of one or two of the cross-coupling partners. The beneficial impact of ...read more
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