Journal of Organic Chemistry p. 7163 - 7171 (1992)
Update date:2022-08-02
Topics:
Dowd, Paul
Zhang, Wei
A new method of appending seven- and eight-membered rings to cycloalkenes is described.Treatment of selected alkene precursors with an ω-bromoalkyl ketene or a keteniminium salt leads to haloalkyl cyclobutanone formation.Tri-n-butyltin hydride promoted ring expansion then yields the annulated product.Since the initial cyclobutanone is cis fused, the final product is also produced stereospecifically with a cis ring fusion.
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Doi:10.1038/nchem.1756
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(1992)