4-Hydroxy-4-phenylthiacyclohexane reacts with methyl bromoacetate to give the product of equatorial approach with high stereoselectivity as shown by the lactonisation method. Similar reactions with methyl iodide and ethyl bromide are also stereoselective; isomerisation reactions indicate that the equatorial products are also formed preferentially.
M. J. Cook, H. Dorn and A. R. Katritzky, J. Chem. Soc. B, 1968, 1467 DOI: 10.1039/J29680001467
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