Addition of Functionalized Nucleophiles to a Bridgehead Bromoketone

Abstract

The reaction of bromoketone 1 with a variety of functionalized organolithiums is presented. In most cases, carbonyl addition followed by quasi-Favorskii rearrangement takes place to afford the rearrangement product in good yield. The utility of products from such a reaction is demonstrated in the synthesis of 22 from 14 via allylation and ring-opening/ring-closing metathesis.

cycloaddition - quasi-Favorskii rearrangement - lithium - metathesis

References

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