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.
N. H. Andersen, H. Uh, S. E. Smith and P. G. M. Wuts, J. Chem. Soc., Chem. Commun., 1972, 956 DOI: 10.1039/C39720000956
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