Effect of BF3·Et2O reagent on the base-promoted rearrangements of epoxides attached to eight-membered rings

Abstract
Cyclooctene oxide 1, cycloocta-1,3-diene oxide 4, and cycloocta-1,5-diene oxide 7 react with organolithium reagents by nucleophilic opening or α- or β-deprotonation. The addition of BF3·Et2O affects the course of the reaction, and also strongly accelerates it. If (−)-sparteine is present, a moderate to high asymmetric induction is obtained.

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