Hydrocyanation of a range of protected β-hydroxyalkynes give unsaturated nitriles which can be cyclised to α-alkylidene γ-lactones and in most cases the regioselectivity of hydrocyanation can be controlled giving the desired cyanoalkenes with stereospecific formation of the E-isomer.
W. R. Jackson, P. Perlmutter and A. J. Smallridge, J. Chem. Soc., Chem. Commun., 1985, 1509 DOI: 10.1039/C39850001509
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