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The addition of thiols to methyl propiolate was remarkably accelerated in the presence of alumina to give the Z-isomer of the 1:1 adducts stereoselectively, in which alumina acts as a bifunctional catalyst of acid and base.

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Alumina-Catalyzed Addition of Thiols to Methyl Propiolate.-Although the ratio of the E/Z isomer is dependent on the nature of the solvents, the title addition gives the Z isomer stereoselectively. -(KODOMARI, M.; SAITOH, G.; YOSHITOMI, S.; Bull. Chem. Soc. Jpn. 64 (1991) 11, 3485-3487; Dep. Ind. Chem., Fac. Eng., Shibaura Inst. Technol., Minato, Tokyo 108, Japan; EN)

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