A carbene cascade reaction that constructs functionalized bridged polycyclic ring systems from alkynyl dizaoesters is presented. The alkynyl diazoesters are easily accessible in two steps from commercially available cyclic ketones. The ring size and substitution of substrates control the regio- and diastereoselectivity. Moreover, a bridged heterocyclic product undergoes further transformation into a propellane structure under basic reaction conditions.

Synthesis of bridged polycyclic ring systems via carbene cascades terminating in C–H bond insertion

245th National Meeting (2013)

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