Highly stereoselective boron trifluoride-promoted 5-endo cyclisation of epoxy-allylic stannanes
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 9,p. 2157-2160
- https://doi.org/10.1039/p19910002157
Abstract
A novel and highly stereoselective 5-endo cyclisation of epoxy-allylic stannanes 1 promoted by BF3–Et2O has been discovered. The same reaction occurs with lower regio- and stereo-selectivity via an allylic lithium as a result of transmetallation. The selective formation of trans-3-alkenylcyclopentanols is expected to be of importance in terpenoid syntheses.Keywords
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