Effect of BF3·Et2O reagent on the base-promoted rearrangements of epoxides attached to eight-membered rings
- 2 October 2000
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 20,p. 3354-3355
- https://doi.org/10.1039/b005474g
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.Keywords
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