Stereochemical course of the cyclization of olefinic aldehydes
- 1 January 1972
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 16,p. 956-957
- https://doi.org/10.1039/c39720000956
Abstract
The stereochemistry of the homoallylic alcohols produced in the stannic chloride-catalysed cyclization of aldehydes (Ia), (Ib), and (IX), determined by X-ray crystallography and proton resonance data using lanthanide shift reagents, are consistent with a concerted intramolecular ‘ene reaction’ mechanism for the cyclization and afford the first example of a nearly undistorted twist-chair conformation for a cycloheptane.Keywords
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